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

HRID 1983290Notes

Reaction equation

HRID 1983290 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH:17]1([O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[NH2:25])[CH2:21][CH2:20][CH2:19][CH2:18]1.[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>>[CH:1]1([O:6][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:17]1([O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[NH:25][C:1]([NH:30][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)=[O:6])[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 7298CyclopentanolHCID 738951-Fluoro-2-nitrobenzeneHCID 64853982-(Cyclopentyloxy)aniline2×

Product 2

HCID 221644731-(Cyclopentyloxy)-2-nitrobenzeneYield 80%HCID 59732940N-(2-Cyclopentyloxyphenyl)-N'-(thiazol-2-yl)ureaYield 70%

Procedure

2-(Cyclopentyloxy)-1-nitrobenzene (1.04 g, 80%) was prepared from cyclopentanol (0.46 ml, 5.0 mmol) and 1-fluoro-2-nitrobenzene (0.71 g, 5.0 mmol) following the general procedure G. This was reduced to 2-(cyclopentyloxy)aniline (0.30 g, 68%, 2.5 mmol scale) following general procedure B. N-(2-Cyclopentyloxyphenyl)-N′-(thiazol-2-yl)urea (212 mg, 70%) was prepared from 2-(cyclopentyloxy)aniline (177 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-bd3386ccbfb24114a03cc7dfff7ab811
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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