2-Aminothiazole → 2-(2,3,4-Trimethoxybenzyloxy)-1-nitrobenzene

HRID 598914

Reaction equation

HRID 598914 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5][OH:6].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].[CH3:25][O:26][C:27]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[CH:39]=[CH:38][C:28]=1[CH2:29][O:30][C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[NH2:33].[NH2:46][C:47]1[S:48][CH:49]=[CH:50][N:51]=1>>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH2:5][O:6][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].[CH3:25][O:26][C:27]1[C:41]([O:42][CH3:43])=[C:40]([O:44][CH3:45])[CH:39]=[CH:38][C:28]=1[CH2:29][O:30][C:31]1[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=1[NH:33][C:14]([NH:46][C:47]1[S:48][CH:49]=[CH:50][N:51]=1)=[O:13]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 123571(2,3,4-Trimethoxyphenyl)methanolHCID 669988422-(2,3,4-Trimethoxybenzyloxy)aniline2×

Product 2

HCID 59732707N-[2-(2,3,4-trimethoxybenzyloxy)phenyl]-N'-(thiazol-2-yl)ureaYield 65%HCID 669989102-(2,3,4-Trimethoxybenzyloxy)-1-nitrobenzeneYield 72%

Procedure

2-(2,3,4-Trimethoxybenzyloxy)-1-nitrobenzene (0.46 g, 72%) was prepared from 2,3,4-trimethoxybenzyl alcohol (0.35 ml, 2.0 mmol) and 1-fluoro-2-nitrobenzene (0.21 ml, 2.0 mmol) following the general procedure G. This was reduced to 2-(2,3,4-trimethoxybenzyloxy)aniline (0.26 g, 65%) following the general procedure B. N-[2-(2,3,4-trimethoxybenzyloxy)phenyl]-N′-(thiazol-2-yl)urea (240 mg, 65%) was prepared from 2-(2,3,4-trimethoxybenzyloxy)aniline (0.26 g, 0.9 mmol) and 2-aminothiazole (140 mg, 1.4 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-376e2506a5064c158a5bbc7b429937d5
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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