2-Aminothiazole → HCID 52466681, compound

HRID 1983264Notes

Reaction equation

HRID 1983264 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].F[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][C:36]=1[F:37])[O:25][C:26]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:27]=1[NH2:28].[NH2:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1>>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[O:9][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[N+:18]([O-:20])=[O:19].[F:21][C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][C:36]=1[F:37])[O:25][C:26]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:27]=1[NH:28][C:4]([NH:38][C:39]1[S:40][CH:41]=[CH:42][N:43]=1)=[O:9]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 677672,5-DifluoronitrobenzeneHCID 759273,4-DifluorophenolHCID 26189682HCID 26189682, compound2×

Product 2

HCID 52466681HCID 52466681, compoundYield 78%HCID 59732900HCID 59732900, compoundYield 72%

Procedure

2-(3,4-Difluorophenoxy)-5-fluoro-1-nitrobenzene (1.05 g, 78%) was prepared from 3,4-difluorophenol (0.72 g, 5.5 mmol) and 2,5-difluoro-1-nitrobenzene (0.8 g, 5.0 mmol) following the general procedure A. This compound was reduced to 2-(3,4-difluorophenoxy)-5-fluoroaniline (0.63 g, 68%) following the general procedure B. N-[2-(3,4-Difluorophenoxy)-5-fluorophenyl]-N′-(thiazol-2-yl)urea (132 mg, 72%) was prepared from 2-(3,4-difluorophenoxy)-5-fluoroaniline (120 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-07ce1698890b403386d80f14d662c77b
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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