2-Aminothiazole → 3-(3-Methyl-butoxy)-4-nitrotoluene

HRID 1983387Notes

Reaction equation

HRID 1983387 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]=CC(N)=[C:15]([O:20][CH2:21]CC(C)C)[CH:14]=1.[NH2:26][C:27]1[S:28][CH:29]=[CH:30][N:31]=1>CC(C)CCO>[CH3:12][CH:13]([CH3:19])[CH2:14][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].[S:28]1[CH:29]=[CH:30][N:31]=[C:27]1[NH:26][C:21](=[O:20])[NH2:8]

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 261895264-Methyl-2-(3-methylbutoxy)aniline2×

Product 2

HCID 167817081-(Thiazol-2-yl)ureaYield 76%HCID 669990283-(3-Methyl-butoxy)-4-nitrotolueneYield 80%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

3-(3-Methyl-butoxy)-4-nitrotoluene (0.89 g, 80%) was prepared from 3-methylbutanol and 3-fluoro-4-nitrotoluene (0.77 g, 5.0 mmol) following the general procedure G. This was reduced to 4-methyl-2-(3-methylbutoxy)aniline (0.55 g, 72%) following general procedure C. 1-[4-Methyl-2-3-methyl-butoxy)-phenyl]-3-thiazol-2-yl-urea (240 mg, 76%) was prepared from 4-methyl-2-(3-methyl-butoxy)aniline (193 mg, 1.0 mmol) and 2-aminothiazole (100 mg, 1.0 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-1ba8134130dc4444986250cc56c26ebb
Source dataset
uspto-grants-2009_06
Patent number
US07541373B2

Reaction notes

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