5-Ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione (Phenobarbital) [C12H12N2O3]

Page 1

Reaxys

PubChem

eMolecules

Bioactivities (2744)

Yield

LabNetwork

SigmaAldrich

Reactions (25)

Substances (31)

Targets (183)

Conditions

Citations (33)

References

1

Synthesize Find similar 24%

Synthesize Find similar

Rx-ID: 21942163 Find similar reactions

in acetonitrile

Electrolysis;

Stalder, Romain; Roth, Gregory P.

ACS Medicinal Chemistry Letters, 2013 , vol. 4, # 11 p. 1119 - 1123 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 2 steps 1: 22 percent / CrO3 / acetic acid / 0.17 h / 20 °C 2: 38 percent / CrO3 / acetic acid / 0.17 h / 20 °C View Scheme

Lafont; Cave; Menager; Miocque

European Journal of Medicinal Chemistry, 1990 , vol. 25, # 1 p. 61 - 66 Title/Abstract Full Text View citing articles Show Details


2

Synthesize Find similar 5-Aethyl-5-phenyl-<2-14C>barbitursaeure;

Rx-ID: 5504415 Find similar reactions

Cacace; Montefinale

Ricerca Scientifica, 1958 , vol. 28, p. 1419,1421 Full Text View citing articles Show Details

Okui; Kuroiwa

Chemical and Pharmaceutical Bulletin, 1963 , vol. 11, p. 163,165 Full Text View citing articles Show Details

Brandstaetter-Kuhnert

Scientia Pharmaceutica, 1960 , vol. 28, p. 150 Chem.Abstr., 1960 , # 23197 Full Text View citing articles Show Details

Shimo; Wakamatsu

Kogyo Kagaku Zasshi, 1960 , vol. 63, p. 2150,2151 Chem.Abstr., vol. 58, # 2452 Full Text View citing articles Show Details

Spassov; Raikov

Zeitschrift fuer Chemie (Stuttgart, Germany), 1971 , vol. 11, p. 260 Full Text View citing articles Show Details

Neville

Analytical Chemistry, 1970 , vol. 42, p. 347,349 Full Text View citing articles Show Details

Kuhnert-Brandstätter; Bachleitner-Hofmann

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1971 , vol. 304, # 8 p. 580 - 590 Title/Abstract Full Text View citing articles Show Details

Stajer et al.

Archiv der Pharmazie (Weinheim, Germany), 1977 , vol. 310, p. 326,328,329 Full Text View citing articles Show Details

Vida; Hooker; Reinhard

Journal of Medicinal Chemistry, 1973 , vol. 16, p. 602 - 605 Title/Abstract Full Text View citing articles Show Details

Fuerst; Hendel

Patent: DD60038 , 1968 ; Chem.Abstr., 1969 , vol. 70, # 68415q Full Text Show Details

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.

Patent: HU154226 , 1966 ; Chem.Abstr., 1968 , vol. 69, # 36159x Full Text Show Details

Mesley; Clements; Flaherty; Goodhead

The Journal of pharmacy and pharmacology, 1968 , vol. 20, # 5 p. 329 - 340 Title/Abstract Full Text View citing articles Show Details

Bojarski; Kahl

Roczniki Chemii, 1967 , vol. 41, # 2 p. 311 Full Text Show Details

Hide Experimental Procedure

Hyperion, Inc.

Patent: US6060598 A1, 2000 ; Title/Abstract Full Text Show Details

13.C:C. C. Preparation of Probe The phenobarbital probe was prepared as follows: 1.2 mg of 5-ethyl-5-(aminophenyl)barbituric acid (P-aminophenobarbital) was placed in a 3.0 ml reaction vial and dissolved with 200 μl DMF. In a separate vial the caged dicarboxy silicon phthalocyanine (1.0 mg) was dissolved in 200 μl DMF and then transferred to the reaction vial. To the reaction vial was added 2.4 mg HOBT, dissolved and mixed well. To make the final reaction mixture, 2.8 mg of EDAC was added and mixed thoroughly. The reaction mixture was stored overnight at about 4 to 8° C.


A

B

Synthesize Find similar

Synthesize Find similar

3

Rx-ID: 24467069 Find similar reactions

Research Development Corp. of Japan; Stanley Electric Co., Ltd.

Patent: US5354563 A1, 1994 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

3:EXAMPLE 3

Phenobarbital: m.p. 174°-178° C. (sedative, hypnotic, antiepileptic; crystalline powder) Phenobarbital Sodium:

4

Synthesize Find similar 38%

Synthesize Find similar

With chromium(VI) oxide in acetic acid

T=20°C; 0.166667 h;

Rx-ID: 2228097 Find similar reactions

Lafont; Cave; Menager; Miocque

European Journal of Medicinal Chemistry, 1990 , vol. 25, # 1 p. 61 - 66 Title/Abstract Full Text View citing articles Show Details

5

Synthesize Find similar

Rx-ID: 748306 Find similar reactions

14%

With N(Et)4ClO4 in N,N-dimethyl-formamide

Ambient temperatureelectrolysis;

Synthesize Find similar

Synthesize Find similar

Arai; Tamura; Kawai; Nakajima

Chemical and Pharmaceutical Bulletin, 1989 , vol. 37, # 11 p. 3117 - 3118 Title/Abstract Full Text View citing articles Show Details


With sodium ethanolate

Bayer and Co.

Patent: DE247952 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 926 Full Text Show Details

6

Synthesize Find similar

Rx-ID: 1795502 Find similar reactions

91%

Synthesize Find similar

Synthesize Find similar

With pyridine in chloroform

T=40°C; 4 h;

Kopinski, Richard P.; Pinhey, John T.; Rowe, Bruce A.

Australian Journal of Chemistry, 1984 , vol. 37, # 6 p. 1245 - 1254 Title/Abstract Full Text Show Details

With pyridine in chloroform

T=40°C; Yield given;

Pinhey, John T.; Rowe, Bruce A.

Tetrahedron Letters, 1980 , vol. 21, p. 965 - 968 Title/Abstract Full Text View citing articles Show Details

A

B

Synthesize Find similar

Synthesize Find similar

7

Synthesize Find similar Rx-ID: 2098871 Find similar reactions

metabolism study in epileptic fowl;

8

Johnson; Davis

Arzneimittel-Forschung/Drug Research, 1984 , vol. 34, # 12 p. 1753 - 1757 Title/Abstract Full Text View citing articles Show Details


Synthesize Find similar

Synthesize Find similar

Rx-ID: 2127434 Find similar reactions

64%

With hydrogenchloride; sodium nitrite in dichloromethane; water

T=45°C; 1.5 h;

Joergensen, K. A.; Ghattas, A.-B.A.G.; Lawesson, S.-O.

Tetrahedron, 1982 , vol. 38, # 9 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details

10%

With tert-butylhypochlorite in tetrachloromethane; ethanol

T=40°C; 8 h;

El-Wassimy, M.T.M.; Jorgensen, K.A.; Lawesson, S.-O.

Tetrahedron, 1983 , vol. 39, # 10 p. 1729 - 1734 Title/Abstract Full Text View citing articles Show Details

A

B

C

Synthesize Find similar

Synthesize Find similar

Synthesize Find similar

9

Synthesize Find similar Rx-ID: 3498179 Find similar reactions

A: 85% B: 5% C: 4%

in ethanol

T=70°C; various pH, temp., Ea; KineticsRate constantProduct distribution;

Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek

Polish Journal of Chemistry, 1983 , vol. 57, # 7-9 p. 799 - 807 Title/Abstract Full Text Show Details

A: 85% B: 5% C: 4%

in sodium hydroxide

T=70°C; 8 h;

Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek

Polish Journal of Chemistry, 1983 , vol. 57, # 7-9 p. 799 - 807 Title/Abstract Full Text Show Details

A

B

C

Synthesize

Synthesize

Synthesize

10

Synthesize Find similar


Rx-ID: 3498180 Find similar reactions

A: 30% B: 40%

Find similar

Find similar

Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek

Polish Journal of Chemistry, 1983 , vol. 57, # 7-9 p. 799 - 807 Title/Abstract Full Text Show Details

T=70°C; 8 h; buffer pH 13;

11

Synthesize Find similar

Rx-ID: 25269543 Find similar reactions

Synthesize Find similar

With CaCl2; sodium hydrogencarbonate in methanol; water; N,N-dimethyl-formamide

Hide Experimental Procedure

Synthesize Find similar

Syva Company

Patent: US3966744 A1, 1976 ; Title/Abstract Full Text Show Details

4.1.B:N-Carboxymethyl phenobarbitone

B. A solution of sodium phenobarbitone (8.8 g, 35 mmoles), and sodium chloroacetate (4.5 g, 38 mmoles) in methanol (250 ml) was mixed with a solution of CaCl2 (3 g) in methanol (50 ml). After addition of 5 ml DMF the mixture was refluxed for 36 hours. After removal of the solvent, the residue was treated with water (100 ml) and acidified with conc. HCl followed by extraction with chloroform. The organic layer was evaporated to dryness and the residue treated with 10percent NaHCO3 solution. Extraction with chloroform and evaporation of the organic layer yielded 3 g of unreacted phenobarbital. The bicarbonate layer was acidified with conc. HCl and extracted with chloroform.

12

Synthesize Find similar With sulfuric acid

Find similar

Synthesize Find similar

Rx-ID: 345111 Find similar reactions

Dvornik et al.

Arhiv za Kemiju, 1954 , vol. 26, p. 15,17 Full Text View citing articles Show Details


13

Synthesize Find similar

Synthesize Find similar

With sulfuric acid

Rx-ID: 398954 Find similar reactions

Dvornik et al.

Arhiv za Kemiju, 1954 , vol. 26, p. 15,17 Full Text View citing articles Show Details

14

Synthesize Find similar

Synthesize Find similar

Rx-ID: 22315546 Find similar reactions

Multi-step reaction with 2 steps 2: aqueous H2SO4

View Scheme

Dvornik et al.

Arhiv za Kemiju, 1954 , vol. 26, p. 15,17 Full Text View citing articles Show Details

Multi-step reaction with 2 steps 2: aqueous H2SO4

View Scheme

Dvornik et al.

Arhiv za Kemiju, 1954 , vol. 26, p. 15,17 Full Text View citing articles Show Details

15

Synthesize Find similar With hydrogenchloride

Synthesize Find similar

Rx-ID: 330211 Find similar reactions

Chamberlain et al.

Journal of the American Chemical Society, 1935 , vol. 57, p. 352 Full Text View citing articles Show Details


16

Synthesize Find similar

Synthesize Find similar

Multi-step reaction with 3 steps 1: diethyl ether 2: ethanol 3: aqueous HCl View Scheme

Rx-ID: 22312727 Find similar reactions

Chamberlain et al.

Journal of the American Chemical Society, 1935 , vol. 57, p. 352 Full Text View citing articles Show Details

17

Synthesize Find similar

Synthesize Find similar

Multi-step reaction with 2 steps 1: ethanol 2: aqueous HCl View Scheme

Rx-ID: 22314752 Find similar reactions

Chamberlain et al.

Journal of the American Chemical Society, 1935 , vol. 57, p. 352 Full Text View citing articles Show Details

18

Synthesize Find similar

Synthesize Find similar

Rx-ID: 5504417 Find similar reactions

Nelson; Cretcher

Journal of the American Chemical Society, 1928 , vol. 50, p. 2761 Full Text View citing articles Show Details


19

Synthesize Find similar

Rx-ID: 747286 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Synthesize Find similar

Rising; Stieglitz

Journal of the American Chemical Society, 1918 , vol. 40, p. 728 Full Text Show Details

20

Synthesize Find similar

Rx-ID: 747973 Find similar reactions

Synthesize Find similar

With sodium methylate

T=105 - 108°C; im Rohr;

Synthesize Find similar

Rising; Stieglitz

Journal of the American Chemical Society, 1918 , vol. 40, p. 728 Full Text Show Details

21

Synthesize Find similar

Rx-ID: 262076 Find similar reactions

With sodium hydroxide

T=100°C; im Rohr;

Synthesize Find similar

Synthesize Find similar

Bayer and Co.

Patent: DE247952 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 926 Full Text Show Details

Synthesize Find similar


22

Synthesize Find similar

Synthesize Find similar

With hydrogenchloride

Rx-ID: 375833 Find similar reactions

Bayer and Co.

Patent: DE249722 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 929 Full Text Show Details

23

Synthesize Find similar

Rx-ID: 748305 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Synthesize Find similar

Bayer and Co

Patent: DE247952 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 926 Full Text Show Details

24

Synthesize Find similar

Rx-ID: 5504416 Find similar reactions

Synthesize Find similar

Synthesize Find similar

Bayer and Co.

Patent: DE249722 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 928 Full Text Show Details

Synthesize Find similar


25

Synthesize Find similar Multi-step reaction with 2 steps 1: sodium ethylate / 100 °C / im Rohr 2: NaOH-solution / 100 °C / im Rohr View Scheme

Synthesize Find similar

Rx-ID: 22314686 Find similar reactions

Bayer and Co.

Patent: DE247952 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 11, p. 926 Full Text Show Details


Turn static files into dynamic content formats.

Create a flipbook
Issuu converts static files into: digital portfolios, online yearbooks, online catalogs, digital photo albums and more. Sign up and create your flipbook.