1-Butanol → 2-Butoxy-4-methyl-1-nitrobenzene

HRID 1983386Notes

Reaction equation

HRID 1983386 reaction equation
F[C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[C:15]([O:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH:14]=1.[NH2:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1.[CH2:31]([OH:35])CCC>>[CH2:15]([O:20][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[CH2:14][CH2:13][CH3:12].[CH2:21]([O:20][C:15]1[CH:14]=[C:13]([CH3:12])[CH:19]=[CH:18][C:16]=1[NH:17][C:31]([NH:25][C:26]1[S:27][CH:28]=[CH:29][N:30]=1)=[O:35])[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 2631-ButanolHCID 21552-AminothiazoleHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 247089402-Butoxy-4-methylbenzenamine2×

Product 2

HCID 184742852-Butoxy-4-methyl-1-nitrobenzeneYield 75%HCID 59732836HCID 59732836, compoundYield 70%

Procedure

3-(1-Butoxy)-4-nitrotoluene (0.78 g, 75%) was prepared from 1-butanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 4-methyl-2-(1-butoxy)aniline (0.47 g, 70%) following general procedure C. 1-(2-Butoxy-4-methyl-phenyl)-3-thiazol-2-yl-urea (210 mg, 70%) was prepared from 4-methyl-2-(1-butoxy)aniline (179 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-45491d8713aa4a53b87beda3560a240a
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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