2-Aminothiazole → HCID 12295880, compound

HRID 1983270Notes

Reaction equation

HRID 1983270 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)=[C:28]([CH:30]=1)[NH2:29].[NH2:42][C:43]1[S:44][CH:45]=[CH:46][N:47]=1>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1.[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:31][C:32]2[CH:41]=[CH:40][C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=2)=[C:28]([NH:29][C:2]([NH:42][C:43]2[S:44][CH:45]=[CH:46][N:47]=2)=[O:11])[CH:30]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 86632-NaphtholHCID 677672,5-DifluoronitrobenzeneHCID 12295882HCID 12295882, compound

Product 2

HCID 12295880HCID 12295880, compoundYield 80%HCID 59732927HCID 59732927, compoundYield 65%

Procedure

5-Fluoro-2-(naphth-2-oxy)-1-nitrobenzene (1.13 g, 80%) was prepared from 2-naphthol (0.79 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-(2-naphth-2-oxy)-5-fluoroaniline (0.64 g, 64%) following the general procedure B. N-[5-Fluoro-2-(naphth-2-oxy)phenyl]-N′-(thiazol-2-yl)urea (123 mg, 65%) was prepared from 5-Fluoro-2-(naphth-2-oxy)-aniline (127 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-e5581a936112435da5625a746cd8170f
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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