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25 reactions in Reaxys
2017-12-27 18h:55m:48s (EST)
25 reactions in Reaxys
2017-12-27 18h:59m:05s (EST)
O
1. Query
NH
O
N H
O
Search as: As drawn 2. Query
(1. Query) AND itemno in (1)
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O
O NH O
NH
N H
O
N H
O
Rx-ID: 21942163 View in Reaxys 1/25 Yield
Conditions & References
24%
in acetonitrile, Electrolysis Stalder, Romain; Roth, Gregory P.; ACS Medicinal Chemistry Letters; vol. 4; nb. 11; (2013); p. 1119 - 1123 View in Reaxys Reaction Steps: 2 1: 22 percent / CrO3 / acetic acid / 0.17 h / 20 °C 2: 38 percent / CrO3 / acetic acid / 0.17 h / 20 °C With chromium(VI) oxide in acetic acid Lafont; Cave; Menager; Miocque; European Journal of Medicinal Chemistry; vol. 25; nb. 1; (1990); p. 61 - 66 View in Reaxys
O NH O
N H
O
Rx-ID: 5504415 View in Reaxys 2/25 Yield
Conditions & References 5-Aethyl-5-phenyl-<2-14 C>barbitursaeure Cacace; Montefinale; Ricerca Scientifica; vol. 28; (1958); p. 1419,1421 View in Reaxys Okui; Kuroiwa; Chemical and Pharmaceutical Bulletin; vol. 11; (1963); p. 163,165 View in Reaxys Brandstaetter-Kuhnert; Scientia Pharmaceutica; vol. 28; (1960); p. 150; ; nb. 23197; (1960) View in Reaxys Shimo; Wakamatsu; Kogyo Kagaku Zasshi; vol. 63; (1960); p. 2150,2151; ; vol. 58; nb. 2452 View in Reaxys Spassov; Raikov; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 11; (1971); p. 260 View in Reaxys Neville; Analytical Chemistry; vol. 42; (1970); p. 347,349 View in Reaxys Kuhnert-Brandstätter; Bachleitner-Hofmann; Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft; vol. 304; nb. 8; (1971); p. 580 - 590 View in Reaxys Stajer et al.; Archiv der Pharmazie (Weinheim, Germany); vol. 310; (1977); p. 326,328,329 View in Reaxys Vida; Hooker; Reinhard; Journal of Medicinal Chemistry; vol. 16; (1973); p. 602 - 605 View in Reaxys Patent; Fuerst; Hendel; DD60038; (1968); ; vol. 70; nb. 68415q; (1969) View in Reaxys Patent; Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.; HU154226; (1966); ; vol. 69; nb. 36159x; (1968) View in Reaxys Mesley; Clements; Flaherty; Goodhead; The Journal of pharmacy and pharmacology; vol. 20; nb. 5; (1968); p. 329 - 340 View in Reaxys Bojarski; Kahl; Roczniki Chemii; vol. 41; nb. 2; (1967); p. 311 View in Reaxys 13.C : C. C.
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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. Patent; Hyperion, Inc.; US6060598; (2000); (A1) English View in Reaxys
O
O Na +
NH O
N H
NH O
O
N
O–
Rx-ID: 24467069 View in Reaxys 3/25 Yield
Conditions & References 3 : EXAMPLE 3 Phenobarbital: m.p. 174°-178° C. (sedative, hypnotic, antiepileptic; crystalline powder) Phenobarbital Sodium: Patent; Research Development Corp. of Japan; Stanley Electric Co., Ltd.; US5354563; (1994); (A1) English View in Reaxys
O
O NH
NH O
N H
O
OH
N H
O
Rx-ID: 2228097 View in Reaxys 4/25 Yield
Conditions & References
38 %
With chromium(VI) oxide in acetic acid, Time= 0.166667h, T= 20 °C Lafont; Cave; Menager; Miocque; European Journal of Medicinal Chemistry; vol. 25; nb. 1; (1990); p. 61 - 66 View in Reaxys
O H 2N
O NH 2
O O
NH O O
O
N H
O
Rx-ID: 748306 View in Reaxys 5/25 Yield 14 %
Conditions & References With N(Et)4ClO4 in N,N-dimethyl-formamide, Ambient temperature, electrolysis Arai; Tamura; Kawai; Nakajima; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 11; (1989); p. 3117 - 3118 View in Reaxys With sodium ethanolate Patent; Bayer and Co.; DE247952; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 926 View in Reaxys
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O O O
O O
NH
O O
N H
Pb
NH
O
O
O
N H
O
O
Rx-ID: 1795502 View in Reaxys 6/25 Yield
Conditions & References
91 %
With pyridine in chloroform, Time= 4h, T= 40 °C Kopinski, Richard P.; Pinhey, John T.; Rowe, Bruce A.; Australian Journal of Chemistry; vol. 37; nb. 6; (1984); p. 1245 - 1254 View in Reaxys With pyridine in chloroform, T= 40 °C , Yield given Pinhey, John T.; Rowe, Bruce A.; Tetrahedron Letters; vol. 21; (1980); p. 965 - 968 View in Reaxys
O
O
NH 2
O
NH
NH
O O
NH 2
N H
O
N H
O
Rx-ID: 2098871 View in Reaxys 7/25 Yield
Conditions & References metabolism study in epileptic fowl Johnson; Davis; Arzneimittel-Forschung/Drug Research; vol. 34; nb. 12; (1984); p. 1753 - 1757 View in Reaxys
O
O NH
NH O
N H
S
O
N H
O
Rx-ID: 2127434 View in Reaxys 8/25 Yield
Conditions & References
64 %
With hydrogenchloride, sodium nitrite in dichloromethane, water, Time= 1.5h, T= 45 °C Joergensen, K. A.; Ghattas, A.-B.A.G.; Lawesson, S.-O.; Tetrahedron; vol. 38; nb. 9; (1982); p. 1163 - 1168 View in Reaxys
10 %
With tert-butylhypochlorite in tetrachloromethane, ethanol, Time= 8h, T= 40 °C El-Wassimy, M.T.M.; Jorgensen, K.A.; Lawesson, S.-O.; Tetrahedron; vol. 39; nb. 10; (1983); p. 1729 - 1734 View in Reaxys
O
O
H N
O
H N
N
O O
N H
O NH
O
HO
O
O
O
N H
O
Rx-ID: 3498179 View in Reaxys 9/25 Yield
Conditions & References
85 %, 5 %, in ethanol, T= 70 °C , various pH, temp., Ea, Kinetics, Rate constant, Product distribution 4% Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek; Polish Journal of Chemistry; vol. 57; nb. 7-9; (1983); p. 799 - 807 View in Reaxys
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85 %, 5 %, in sodium hydroxide, Time= 8h, T= 70 °C 4% Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek; Polish Journal of Chemistry; vol. 57; nb. 7-9; (1983); p. 799 - 807 View in Reaxys
O
O
O
H N
O N
NH 2 O
O NH
N H
HO
O
O
O
N H
O
Rx-ID: 3498180 View in Reaxys 10/25 Yield
Conditions & References
30 %, 40 %
Time= 8h, T= 70 °C , buffer pH 13 Paluchowska, Maria; Ekiert, Leszek; Jochym, Krystyna; Bojarski, Jacek; Polish Journal of Chemistry; vol. 57; nb. 7-9; (1983); p. 799 - 807 View in Reaxys
O
O
O
Cl
Na
Na +
+
NH
NH
O– O
N
O
O–
N H
O
Rx-ID: 25269543 View in Reaxys 11/25 Yield
Conditions & References 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. With CaCl2, sodium hydrogencarbonate in methanol, water, N,N-dimethyl-formamide Patent; Syva Company; US3966744; (1976); (A1) English View in Reaxys
O
O
NH
NH O
N
NH 2
O
N H
O
Rx-ID: 345111 View in Reaxys 12/25 Yield
Conditions & References With sulfuric acid Dvornik et al.; Arhiv za Kemiju; vol. 26; (1954); p. 15,17 View in Reaxys
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O
O
N
NH
N O
N
O
NH 2
N H
O
Rx-ID: 398954 View in Reaxys 13/25 Yield
Conditions & References With sulfuric acid Dvornik et al.; Arhiv za Kemiju; vol. 26; (1954); p. 15,17 View in Reaxys
O
O O
NH O
O
O
N H
O
Rx-ID: 22315546 View in Reaxys 14/25 Yield
Conditions & References Reaction Steps: 2 2: aqueous H2SO4 With sulfuric acid Dvornik et al.; Arhiv za Kemiju; vol. 26; (1954); p. 15,17 View in Reaxys Reaction Steps: 2 2: aqueous H2SO4 With sulfuric acid Dvornik et al.; Arhiv za Kemiju; vol. 26; (1954); p. 15,17 View in Reaxys
O
O
NH
NH H 2N
N
O
O
N H
O
Rx-ID: 330211 View in Reaxys 15/25 Yield
Conditions & References With hydrogenchloride Chamberlain et al.; Journal of the American Chemical Society; vol. 57; (1935); p. 352 View in Reaxys
N O
Na +
O
NH
O– O
N H
O
Rx-ID: 22312727 View in Reaxys 16/25 Yield
Conditions & References Reaction Steps: 3 1: diethyl ether 2: ethanol 3: aqueous HCl With hydrogenchloride, diethyl ether, ethanol
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Chamberlain et al.; Journal of the American Chemical Society; vol. 57; (1935); p. 352 View in Reaxys
N
O O
NH O
O
N H
O
Rx-ID: 22314752 View in Reaxys 17/25 Yield
Conditions & References Reaction Steps: 2 1: ethanol 2: aqueous HCl With hydrogenchloride, ethanol Chamberlain et al.; Journal of the American Chemical Society; vol. 57; (1935); p. 352 View in Reaxys
H 2N
O
O
ethylphenyl-malonic acid ester
NH 2
NH O
N H
O
Rx-ID: 5504417 View in Reaxys 18/25 Yield
Conditions & References Nelson; Cretcher; Journal of the American Chemical Society; vol. 50; (1928); p. 2761 View in Reaxys
O O –O
HO
H 2N
Na +
O
O
O
NH
NH 2
O
O
N H
O
Rx-ID: 747286 View in Reaxys 19/25 Yield
Conditions & References Rising; Stieglitz; Journal of the American Chemical Society; vol. 40; (1918); p. 728 View in Reaxys
O O
H 2N
O
O
O
NH
NH 2
O
O
N H
O
Rx-ID: 747973 View in Reaxys 20/25 Yield
Conditions & References With sodium methylate, T= 105 - 108 °C , im Rohr Rising; Stieglitz; Journal of the American Chemical Society; vol. 40; (1918); p. 728 View in Reaxys
O
O
Br
NH O
N H
NH
O
O
N H
O
Rx-ID: 262076 View in Reaxys 21/25
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Yield
Conditions & References With sodium hydroxide, T= 100 °C , im Rohr Patent; Bayer and Co.; DE247952; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 926 View in Reaxys
O
O
NH O
N H
NH
O
O
N H
O
Rx-ID: 375833 View in Reaxys 22/25 Yield
Conditions & References With hydrogenchloride Patent; Bayer and Co.; DE249722; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 929 View in Reaxys
O H 2N
O– Na +
OH
O
O O
NH
NH 2
O
O
O
N H
O
Rx-ID: 748305 View in Reaxys 23/25 Yield
Conditions & References Patent; Bayer and Co; DE247952; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 926 View in Reaxys
O
Cl
H
O
NH O
N
NH
O
O
N H
O
Rx-ID: 5504416 View in Reaxys 24/25 Yield
Conditions & References Patent; Bayer and Co.; DE249722; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 928 View in Reaxys
O O
O
NH
O O
O
N H
O
Rx-ID: 22314686 View in Reaxys 25/25 Yield
Conditions & References Reaction Steps: 2 1: sodium ethylate / 100 °C / im Rohr 2: NaOH-solution / 100 °C / im Rohr With sodium hydroxide, sodium ethanolate Patent; Bayer and Co.; DE247952; Fortschr. Teerfarbenfabr. Verw. Industriezweige; vol. 11; p. 926 View in Reaxys
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