Isobutanol → 4-Methyl-2-(2-methylpropoxy)aniline

HRID 2276158Notes

Reaction equation

HRID 2276158 reaction equation
[CH3:1][CH:2]([CH3:5])[CH2:3][OH:4].F[C:7]1[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]>>[CH3:1][CH:2]([CH3:5])[CH2:3][O:4][C:7]1[CH:8]=[C:9]([CH3:16])[CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14].[CH3:16][C:9]1[CH:10]=[CH:11][C:12]([NH2:13])=[C:7]([O:4][CH2:3][CH:2]([CH3:5])[CH3:1])[CH:8]=1

Participants

4

Reactant 2

HCID 6560IsobutanolHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

Product 2

HCID 246935594-Methyl-2-(2-methylpropoxy)anilineHCID 525421862-Isobutoxy-4-methyl-1-nitrobenzene

Procedure

3-(2-Methylpropoxy)-4-nitrotoluene (0.78 g) is prepared from 2-methylpropanol (0.46 ml, 5.0 mmol) and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This is reduced to afford 4-methyl-2-(2-methylpropoxy)aniline (0.47 g) following general procedure C. N-[4-Methyl-2-(2-methylpropoxy)phenyl]-N′-(thiazol-2-yl)urea (210 mg) is prepared from 4-methyl-2-(2-methylpropoxy)aniline (179 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-807f983d8b79479b926cb33f88edc063
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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