2-Aminothiazole → HCID 13514833, compound

HRID 559842Notes

Reaction equation

HRID 559842 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].F[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[Cl:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[Cl:35])[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH2:27].[NH2:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[O:9][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-:19])=[O:18].[Cl:20][C:21]1[CH:22]=[C:23]([CH:32]=[CH:33][C:34]=1[Cl:35])[O:24][C:25]1[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=1[NH:27][C:4]([NH:36][C:37]1[S:38][CH:39]=[CH:40][N:41]=1)=[O:9]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 72583,4-DichlorophenolHCID 738951-Fluoro-2-nitrobenzeneHCID 135148342-(3,4-Dichlorophenoxy)benzenamine2×

Product 2

HCID 13514833HCID 13514833, compoundYield 81%HCID 59733139HCID 59733139, compoundYield 68%

Procedure

2-(3,4-Dichlorophenoxy)-1-nitrobenzene (1.15 g, 81%) was prepared from 3,4-dichlorophenol (0.9 g, 5.5 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure A. This was reduced to 2-(3,4-dichlorophenoxy)aniline (0.69 g, 68%) following general procedure B. N-[2-(3,4-Dichlorophenoxy)phenyl]-N′-(thiazol-2-yl)urea (129 mg, 68%) was prepared from 2-(3,4-dichlorophenoxy)aniline (127 mg, 0.5 mmol) and 2-aminothiazole (60 mg, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-225e936985e94c3faaa722fbde2db639
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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