2-Aminothiazole → 2-(2-Methoxyphenylsulfanyl)nitrobenzene

HRID 131848

Reaction equation

HRID 131848 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH:31][C:1]([NH:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1)=[O:2]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 23642ThioguaiacolHCID 738951-Fluoro-2-nitrobenzeneHCID 209806312-(2-Methoxyphenylsulfanyl)aniline2×

Product 2

HCID 8249072-(2-Methoxyphenylsulfanyl)nitrobenzeneYield 82%HCID 59733084N-[2-(2-Methoxyphenylsulfanyl)phenyl]-N'-(thiazol-2-yl)ureaYield 62%

Procedure

2-(2-Methoxyphenylsulfanyl)nitrobenzene (1.07 g, 82%) was prepared from 2-methoxy thiophenol (0.76 g, 5.5 mmol) and 2-fluoronitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2-methoxyphenylsulfanyl)aniline (0.66 g, 70%) following general procedure B. N-[2-(2-Methoxyphenylsulfanyl)phenyl]-N′-(thiazol-2-yl)urea (110 mg, 62%) was prepared from 2-(2-methoxyphenylsulfanyl)aniline (115 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-e67c8779f6fe4457b8596b100dca7ece
Source dataset
uspto-grants-2008_06
Patent number
US07384967B2

Linked notes

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