Query Query HS
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13 reactions in Reaxys
2018-06-12 19h:58m:43s (UTC)
Search as: Product, As drawn, No mixtures ) AND (RX.PXRN=2040351)))
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H 2N
HS
Rx-ID: 1360096 View in Reaxys 1/13 Yield
Conditions & References (i) aq. NaNO2, aq. HCl, (ii) potassium ethylxanthate, (iii) KOEt, EtOH, Multistep reaction Godt,H.C.; Wann,R.E.; Journal of Organic Chemistry; vol. 26; (1961); p. 4047 - 4051 View in Reaxys (i) NaNO2, aq. HCl, (ii) aq. EtOCS2K, Multistep reaction Patent; Lilly, Eli, and Co.; FR1481052; (1967) French; ; vol. 69; nb. 18840; (1968) View in Reaxys Reaction Steps: 2 1: 1. conc. hydrochloric acid, NaNO2; / 1. 0 degC, 30min.; 2. 40 - 45 degC 2: 93 percent / LiAlH4 / diethyl ether / 3 h / Heating With hydrogenchloride, lithium aluminium tetrahydride, sodium nitrite in diethyl ether Tedjamulia, Marvin L.; Tominaga, Yoshinori; Castle, Raymond N.; Journal of Heterocyclic Chemistry; vol. 20; (1983); p. 1485 - 1495 View in Reaxys Reaction Steps: 2 1.1: hydrogenchloride; sodium nitrite / water / 1 h / 0 - 5 °C 1.2: 2 h 2.1: potassium hydroxide / ethanol / 76 - 78 °C With hydrogenchloride, potassium hydroxide, sodium nitrite in ethanol, water Patil, Yogesh; Shingare, Ramesh; Chakraborty, Shakti; Borkute, Rachana; Sarkar, Dhiman; Madje, Balaji; Journal of Chemical Sciences; vol. 130; nb. 3; (2018); Art.No: 22 View in Reaxys
O
S
HS
S
Rx-ID: 2204264 View in Reaxys 2/13 Yield
Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 3h, Heating Tedjamulia, Marvin L.; Tominaga, Yoshinori; Castle, Raymond N.; Journal of Heterocyclic Chemistry; vol. 20; (1983); p. 1485 - 1495 View in Reaxys 2.2a Synthesis of 2, 4 Dimethyl thiophenol (2) In anoven-dried 3-necked round-bottomed flask, a mixture of 2, 4dimethyl aniline (1, 10 g, 82 mmol) in aqueous HCl (50 mL,5N) at 0–5 °Cfollowed by dropwise addition of sodium nitrite(10.5 g, 120 mmol) in water (30 mL). After 1 h, the diazoniumreaction mass was added into potassium ethyl xanthate(19.5 g, 120 mmol), in water (50 mL) solution. The mixturewas heated to 40–45 °C for 2 h. The compound extractedwith MTBE (2×50 mL) and washed with 10percent NaOH solution(80 mL). Organic layer dried over CaCl2 and evaporatedin vacuo to afford 2, 4dimethyl ethyl xanthate (2a). It wasfurther refluxed into ethanolic KOH solution (100 mL in 15gm) for 4–5 h (TLC check with hexane/ethyl acetate 9:1). Thereaction was allowed to cool, quenched with water (400 mL)and evaporated in vacuo. After acid and base treatment andvacuum distillation afforded compound 2. Faint yellow liquid;yield: 8.2 g, 72percent; B.p.: 207–209 °C; IR (Neat) υ: 806(o, p-substituted Ar), 1477 (C=C for Ar) and 2567 (-SH substitutedon Ar) cm−1; 1H NMR (CDCl3): υ 2.27 (s, -CH3),2.30 (s, -CH3), 3.20 (s,-SH), 6.88 (d, J = 8.0 Hz, Ar-H),6.99 (s, Ar-H) and 7.17 (1H, d, J = 8.0 Hz, Ar-H) ppm;13C NMR (CDCl3): υ 20.79, 20.97, 126.86, 127.26, 130.27,131.15, 135.77 and 136.22 ppm; MS (EI): m/z 137agreed forC8H10S [M-H]+ of compound 2.
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With potassium hydroxide in ethanol, T= 76 - 78 °C Patil, Yogesh; Shingare, Ramesh; Chakraborty, Shakti; Borkute, Rachana; Sarkar, Dhiman; Madje, Balaji; Journal of Chemical Sciences; vol. 130; nb. 3; (2018); Art.No: 22 View in Reaxys
N
N
N S
S
S
HS
S
S
S
Rx-ID: 35630339 View in Reaxys 3/13 Yield
Conditions & References With copper(II) perchlorate hexahydrate in [D3]acetonitrile, Mechanism Martínez-Alanis, Paulina R.; Sánchez Eguía, Brenda N.; Ugalde-Saldívar, Víctor M.; Regla, Ignacio; Demare, Patricia; Aullón, Gabriel; Castillo, Ivan; Chemistry - A European Journal; vol. 19; nb. 19; (2013); p. 6067 - 6079 View in Reaxys
O O
HS
S Cl
Rx-ID: 342085 View in Reaxys 4/13 Yield
Conditions & References With ISOPROPYLAMIDE, dimethylsilicon dichloride, zinc in 1,2-dichloro-ethane, Time= 1.5h, T= 75 °C Uchiro, Hiromi; Kobayashi, Susumu; Tetrahedron Letters; vol. 40; nb. 16; (1999); p. 3179 - 3182 View in Reaxys With sulfuric acid, zinc in water, 1.) 0 deg C, 1 h, 2.) reflux, 6 h Faber, Wijnand S.; Kok, Johan; De Lange, Ben; Feringa, Ben L.; Tetrahedron; vol. 50; nb. 16; (1994); p. 4775 - 4794 View in Reaxys With sulfuric acid, zinc Truce; Norman; Journal of the American Chemical Society; vol. 75; (1953); p. 6023 View in Reaxys With sulfuric acid, zinc Uhlenbroek,J.H.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 1057 - 1065 View in Reaxys
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HS
Rx-ID: 18530993 View in Reaxys 5/13 Yield
Conditions & References Reaction Steps: 2 1: chlorosulfonic acid / CHCl3 / 1 h / -5 - 20 °C 2: 69 percent / Zn, H2SO4 / H2O / 1.) 0 deg C, 1 h, 2.) reflux, 6 h With chlorosulfonic acid, sulfuric acid, zinc in chloroform, water Faber, Wijnand S.; Kok, Johan; De Lange, Ben; Feringa, Ben L.; Tetrahedron; vol. 50; nb. 16; (1994); p. 4775 - 4794 View in Reaxys
O
N
S S
O
N
S
P
HO
N
SH HS
P O
Rx-ID: 1811148 View in Reaxys 6/13 Yield
Conditions & References
88 %
in benzene, Time= 2h, Heating, further reaction partners - various diaryl disulfides, Product distribution, Mechanism Oae; Togo; Bulletin of the Chemical Society of Japan; vol. 57; nb. 1; (1984); p. 232 - 236 View in Reaxys
O
HS
Na +
–
O
S O
Rx-ID: 2627193 View in Reaxys 7/13 Yield
Conditions & References With triphenylphosphine, 18-crown-6 ether, iodine in benzene, Time= 41h, Heating Fujimori, Ken; Togo, Hideo; Oae, Shigeru; Tetrahedron Letters; vol. 21; (1980); p. 4921 - 4924 View in Reaxys With 18-crown-6 ether, iodine, triphenylphosphine in benzene, Time= 41h, Heating Oae, Shigeru; Togo, Hideo; Bulletin of the Chemical Society of Japan; vol. 56; nb. 12; (1983); p. 3802 - 3812 View in Reaxys
O O
HS
S HO
Rx-ID: 2040920 View in Reaxys 8/13
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Yield
Conditions & References With diphosphorus pentasulfide, lithium aluminium tetrahydride, 1.) sulfolane, 90 deg C for 24 h 2.) ether, room temperature for 30 min, Yield given. Multistep reaction Oae, Shigeru; Togo, Hideo; Tetrahedron Letters; vol. 23; nb. 45; (1982); p. 4701 - 4704 View in Reaxys
HS
Br
Rx-ID: 2059437 View in Reaxys 9/13 Yield
Conditions & References With sulfur, magnesium, 1.) ether, Multistep reaction Garratt, Dennis G.; Beaulieu, Pierre L.; Canadian Journal of Chemistry; vol. 58; nb. 24; (1980); p. 2738 - 2744 View in Reaxys
HS
Rx-ID: 7244654 View in Reaxys 10/13 Yield
Conditions & References entspr. Aromat, 1) Chlorsulfonsaeure, 2) Reduktion mit Zn, Sn etc. Almasi et al.; Acad. Repub. Pop. Rom., Fil. Cluj, Stud. Cercet. Chim.; vol. 12; nb. 1; (1961); p. 165,166-167 View in Reaxys 2,4-Dimethyl-anilin (diazotiert), 1) Kaliumxanthogenat, 2) alkohol. KOH Morizur; Pallaud; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 253; (1961); p. 494 View in Reaxys 1. 2,4-Dimethyl-anilin, wss. HCl (-> Diazoniumsalz-Lsg.), 2. Kaliumethylxanthogenat 3. ethanol. KOH; Erwaermen Morizur; Bulletin de la Societe Chimique de France; (1964); p. 1331,1336 View in Reaxys 2,4-Dimethyl-1-thiocyanato-benzol, LiAlH4, Ae. <isoliert als (2,4-Dimethyl-phenyl)-(2,4-dinitro-phenyl)-sulfid> Bacon,R.G.R.; Guy,R.G.; Journal of the Chemical Society; (1961); p. 2428 - 2436 View in Reaxys
HS
air
Rx-ID: 22497997 View in Reaxys 11/13 Yield
Conditions & References Reaction Steps: 2 1: ClSO3H 2: Zn, aq. H2SO4 With chlorosulfonic acid, sulfuric acid, zinc Uhlenbroek,J.H.; Recueil des Travaux Chimiques des Pays-Bas; vol. 80; (1961); p. 1057 - 1065 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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HO S
HS
O
Rx-ID: 387354 View in Reaxys 12/13 Yield
Conditions & References With sulfuric acid, zinc Gattermann; Chemische Berichte; vol. 32; (1899); p. 1156 View in Reaxys Lindow; Otto; Justus Liebigs Annalen der Chemie; vol. 146; (1868); p. 237 View in Reaxys Yssel de Schepper; ; (1865); p. 360 View in Reaxys
S
O HS
K+
diazonium chloride from 4-amino-1.3-dimethyl-benzene
S–
Rx-ID: 7244655 View in Reaxys 13/13 Yield
Conditions & References Verseifen des Reaktionsprodukts mit alkoh. Kali Bourgeois; Recueil des Travaux Chimiques des Pays-Bas; vol. 18; (1899); p. 435 View in Reaxys Leuckart; Journal fuer Praktische Chemie (Leipzig); vol. <2> 41; (1890); p. 189 View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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