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

HRID 559900Notes

Reaction equation

HRID 559900 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].F[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[CH3:16][CH:17]([CH3:27])[CH2:18][O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH2:22].[NH2:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1>>[CH3:1][CH:2]([CH3:5])[CH2:3][O:4][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[CH3:16][CH:17]([CH3:27])[CH2:18][O:19][C:20]1[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=1[NH:22][C:3]([NH:28][C:29]1[S:30][CH:31]=[CH:32][N:33]=1)=[O:4]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6560IsobutanolHCID 738951-Fluoro-2-nitrobenzeneHCID 13654662(2-Isobutoxyphenyl)amine2×

Product 2

HCID 122152032-(2-Methylpropoxy)-1-nitrobenzeneYield 75%HCID 47363783N-[2-(2-Methylpropoxy)phenyl]-N'-(thiazol-2-yl)ureaYield 65%

Procedure

2-(2-Methylpropoxy)-1-nitrobenzene (0.73 g, 75%) was prepared from 2-methyl-propanol (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-(2-methylpropoxy)aniline (0.29 g, 70%, 2.5 mmol scale) following general procedure B. N-[2-(2-Methylpropoxy)phenyl]-N′-(thiazol-2-yl)-urea (189 mg, 65%) was prepared from 2-(2-methylpropoxy)aniline (165 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-859a81d0b8ed4352bd39e8f440d0b58a
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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