2-Aminothiazole → 2-Fluoro-5-(2-methylpropoxy)-4-nitrotoluene

HRID 560012Notes

Reaction equation

HRID 560012 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10](F)=[CH:9][C:8]=1[CH3:17].[F:18][C:19]1[C:20]([CH3:31])=[CH:21][C:22]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[C:23]([CH:25]=1)[NH2:24].[NH2:32][C:33]1[S:34][CH:35]=[CH:36][N:37]=1>>[F:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])=[CH:9][C:8]=1[CH3:17].[F:18][C:19]1[C:20]([CH3:31])=[CH:21][C:22]([O:26][CH2:27][CH:28]([CH3:29])[CH3:30])=[C:23]([NH:24][C:3]([NH:32][C:33]2[S:34][CH:35]=[CH:36][N:37]=2)=[O:4])[CH:25]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6560IsobutanolHCID 2306581,4-Difluoro-2-methyl-5-nitrobenzeneHCID 450916065-Fluoro-4-methyl-2-(2-methylpropoxy)aniline2×

Product 2

HCID 597327361-(5-Fluoro-2-isobutoxy-4-methyl-phenyl)-3-thiazol-2-yl-ureaYield 64%HCID 669991632-Fluoro-5-(2-methylpropoxy)-4-nitrotolueneYield 65%

Procedure

2-Fluoro-5-(2-methylpropoxy)-4-nitrotoluene (0.73 g, 65%) was prepared from 2-methylpropanol (0.46 ml, 5.0 mmol) and 2,5-difluoro-4-nitrotoluene (0.86 g, 5.0 mmol) following the general procedure G. This was reduced to 5-fluoro-4-methyl-2-(2-methylpropoxy)-aniline (0.45 g, 70%) following general procedure C. 1-(5-Fluoro-2-isobutoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea (205 mg, 64%) was prepared from 5-fluoro-4-methyl-2-(2-methylpropoxy)-aniline (197 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-4e05f1ae2931468a838910fe4fd874e2
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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