Methyl chloroformate → Methyl N-(3-nitrophenyl)carbamate

HRID 1033149Notes

Reaction equation

HRID 1033149 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].CN(C)C(=O)C.Cl[C:18]([O:20][CH3:21])=[O:19].C(=O)(O)[O-].[Na+]>O>[CH3:21][O:20][C:18]([NH:7][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][CH:8]=1)=[O:19]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 74233-NitroanilineHCID 31374DimethylacetamideHCID 516892Sodium Bicarbonate

Product 1

HCID 4548185Methyl N-(3-nitrophenyl)carbamateYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g of 3-nitroaniline and 100 ml of N,N-dimethylacetamide was stirred under ice cooling and 8.2 g of methyl chloroformate was added dropwise to the mixture. After stirring the mixture for 30 minutes, 300 ml of water was added to the reaction mixture and then the reaction mixture was neutralized by the addition of sodium bicarbonate to deposit crystals, which were recovered by filtration, washed with water, and dried. The amount of the product was 13.1 g (yield: 93%).

Workup

  1. stirringAfter stirring the mixture for 30 minutes
  2. filtrationwere recovered by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-02ca5704a9554fc8a09a32079b8b03eb
Source dataset
uspto-grants-1994_05
Patent number
US05310634

Reaction notes

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