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

HRID 559899

Reaction equation

HRID 559899 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].NC1C=CC=CC=1.[CH:22]([O:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28])([CH3:24])[CH3:23].[NH2:33][C:34]1[S:35][CH:36]=[CH:37][N:38]=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:22]([O:25][C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH:28][C:1]([NH:33][C:34]1[S:35][CH:36]=[CH:37][N:38]=1)=[O:4])([CH3:24])[CH3:23]

Participants

7

Reactant 5

HCID 21552-AminothiazoleHCID 3776IsopropanolHCID 6115AnilineHCID 344362-(1-Methylethoxy)benzenamineHCID 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-9f38056949b142a48ce5a36ca9e72e96
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Linked notes

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