2-Aminothiazole → 3-Cyclopentylmethoxy-4-nitrotoluene

HRID 599090

Reaction equation

HRID 599090 reaction equation
[CH:1]1([CH2:6][OH:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:9]1[CH:10]=[C:11]([CH3:18])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].[CH:19]1([CH2:24][O:25][C:26]2[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:27]=2[NH2:28])[CH2:23][CH2:22][CH2:21][CH2:20]1.[NH2:34][C:35]1[S:36][CH:37]=[CH:38][N:39]=1>>[CH:1]1([CH2:6][O:7][C:9]2[CH:10]=[C:11]([CH3:18])[CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:19]1([CH2:24][O:25][C:26]2[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:27]=2[NH:28][C:6]([NH:34][C:35]2[S:36][CH:37]=[CH:38][N:39]=2)=[O:7])[CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 77195CyclopentanemethanolHCID 261895182-(Cyclopentylmethoxy)-4-methylaniline2×

Product 2

HCID 597328301-(2-Cyclopentylmethoxy-4-methyl-phenyl)-3-thiazol-2-yl-ureaYield 68%HCID 669989813-Cyclopentylmethoxy-4-nitrotolueneYield 70%

Procedure

3-Cyclopentylmethoxy-4-nitrotoluene (0.82 g, 70%) was prepared from cyclopentylmethanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 2-cyclopentylmethoxy-4-methyl-aniline (0.58 g, 81%) following general procedure C. 1-(2-Cyclopentylmethoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea (225 mg, 68%) was prepared from 2-cyclopentylmethoxy-4-methyl-aniline (205 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-4d23c0c9c7c44b9d8c759c8de255bb33
Source dataset
uspto-grants-2011_03
Patent number
US07897628B2

Linked notes

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