Potassium Carbonate → Tert-butyl [3-methyl-3-(5-methyl-2-nitro-phenylamino)-butyl]-carbamate

HRID 33365Notes

Reaction equation

HRID 33365 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].[NH2:12][C:13]([CH3:25])([CH3:24])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:25][C:13]([NH:12][C:2]1[CH:3]=[C:4]([CH3:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])([CH3:24])[CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-HCID 45072486tert-butyl N-(3-amino-3-methylbutyl)carbamate

Product 1

HCID 86603965Tert-butyl [3-methyl-3-(5-methyl-2-nitro-phenylamino)-butyl]-carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.0 g (12.9 mmol) 3-fluoro-4-nitro-toluene, 2.6 g (13.0 mmol) tert-butyl (3-amino-3-methyl-butyl)-carbamate and 2.3 g (16.8 mmol) potassium carbonate are stirred overnight at ambient temperature in 20 mL DMF. The solvent is distilled off and the residue is combined with ethyl acetate. The mixture is washed repeatedly with water, dried with sodium sulphate and the solvent is eliminated. 4.8 g yellow oil. Mass spectroscopy: [M+H]+=338.

Workup

  1. distillationThe solvent is distilled off
  2. washThe mixture is washed repeatedly with water
  3. dry with materialdried with sodium sulphate

Sources & evidence

ORD record
ord-0f0c11cfd1dc4952bf8cc9718579b0c3
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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