2-Aminothiazole → HCID 66998767, compound

HRID 2276111Notes

Reaction equation

HRID 2276111 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[OH:13].F[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([O:42][CH3:43])=[O:41])[C:27]=1[O:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH2:31].[NH2:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1>>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=1[O:13][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22].[CH3:24][O:25][C:26]1[CH:39]=[CH:38][CH:37]=[C:36]([C:40]([O:42][CH3:43])=[O:41])[C:27]=1[O:28][C:29]1[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=1[NH:31][C:4]([NH:44][C:45]1[S:46][CH:47]=[CH:48][N:49]=1)=[O:13]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 738951-Fluoro-2-nitrobenzeneHCID 80651Methyl 3-methoxysalicylateHCID 669988122-(2-Methoxy-6-methoxycarbonylphenoxy)aniline2×

Product 2

HCID 59732930HCID 59732930, compoundYield 72%HCID 66998767HCID 66998767, compoundYield 82%

Procedure

2-(2-Methoxy-6-methoxycarbonylphenoxy)-1-nitrobenzene (1.24 g, 82%) was prepared from methyl 3-methoxysalicylate (1.0 g, 5.5 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(2-methoxy-6-methoxycarbonylphenoxy)aniline (0.89 g, 80%) following the general procedure C. N-[2-(2-Methoxy-6-methoxycarbonylphenoxy)phenyl]-N′-(thiazol-2-yl)urea (143 mg, 72%) was prepared from 2-(2-methoxy-6-methoxycarbonylphenoxy)aniline (136 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-89392c629fc24ed6a20f4ac1546fb11b
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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