2-Aminothiazole → 1-(1-Methylethoxy)-2-nitrobenzene

HRID 598983

Reaction equation

HRID 598983 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].F[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13].[CH:15]([O:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH2:21])([CH3:17])[CH3:16].[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1>>[CH:1]([O:4][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])([CH3:3])[CH3:2].[CH:15]([O:18][C:19]1[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=1[NH:21][C:1]([NH:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1)=[O:4])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 3776IsopropanolHCID 344362-(1-Methylethoxy)benzenamine2×HCID 738951-Fluoro-2-nitrobenzene

Product 2

HCID 1971801-(1-Methylethoxy)-2-nitrobenzeneYield 70%HCID 47363733N-(2-Isopropoxyphenyl)-N'-thiazolylureaYield 60%

Procedure

2-(Isopropoxy)-1-nitrobenzene (317 mg, 70%) was prepared from isopropyl alcohol (0.24 ml, 3.0 mmol) and 1-fluoro-2-nitrobenzene (0.36 g, 2.5 mmol) following the general procedure G. This was reduced to 2-(isopropoxy)aniline (198 mg, 75%) following general procedure B. N-(2-Isopropoxyphenyl)-N′-thiazolylurea (218 mg, 60%) was prepared from 2-(isopropoxy)aniline (198 mg, 01.3 mmol) and 2-aminothiazole (150 mg, 1.5 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-05e2bb222c9d4080987aa2ec97d74d5c
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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