2-Aminothiazole → 1-Fluoro-4-(2-methylpropoxy)-2-nitrobenzene

HRID 1983403Notes

Reaction equation

HRID 1983403 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].F[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[C:10]([F:16])=[CH:9][CH:8]=1.[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:22]([CH:24]=1)[NH2:23].[NH2:30][C:31]1[S:32][CH:33]=[CH:34][N:35]=1>>[F:16][C:10]1[C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])=[CH:8][CH:9]=1.[F:17][C:18]1[CH:19]=[CH:20][C:21]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[C:22]([NH:23][C:3]([NH:30][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)=[O:4])[CH:24]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6560IsobutanolHCID 677672,5-DifluoronitrobenzeneHCID 284122165-Fluoro-2-(2-methylpropoxy)aniline2×

Product 2

HCID 59733029HCID 59733029, compoundYield 72%HCID 669989321-Fluoro-4-(2-methylpropoxy)-2-nitrobenzeneYield 78%

Procedure

5-Fluoro-2-(2-methylpropoxy)-4-nitrobenzene (0.83 g, 78%) was prepared from 2-methylpropanol (0.46 ml, 5.0 mmol) and 2,5-difluoro-4-nitrobenzene (0.80 g, 5.0 mmol) following the general procedure G. This was reduced to 5-fluoro-2-(2-methylpropoxy)-aniline (0.58 g, 81%) following general procedure C. 1-(5-Fluoro-2-isobutoxy-phenyl)-3-thiazol-2-yl-urea (220 mg, 72%) was prepared from 5-fluoro-2-(2-methylpropoxy)-aniline (183 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-284963f72f0543eaa1045c435a419122
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

Loading…