Diisopropylamine → phenyl N-(4-methoxy-2-nitrophenyl)carbamate

HRID 1901052Notes

Reaction equation

HRID 1901052 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1.C(NC(C)C)(C)C.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:27](=[O:28])[O:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 15891Phenyl chloroformateHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 16227844phenyl N-(4-methoxy-2-nitrophenyl)carbamateYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methoxy-2-nitroaniline (15.0 g) and diisopropylamine (16.2 ml) in dichloromethane (300 ml) was added dropwise under ice-cooling a solution of phenylchloroformate (16.8 g) in dichloromethane (30 ml). The reaction solution was stirred at room temperature overnight, washed with water and saturated saline and dried over anhydrous MgSO4. The solvent was distilled off. Crystallization of the residue from hexane gave phenyl 4-methoxy-2-nitrophenylcarbamate (12.6 g, 49.1%) as crystals.

Workup

  1. washwashed with water and saturated saline
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was distilled off
  4. customCrystallization of the residue from hexane

Sources & evidence

ORD record
ord-88f10e09a21343cabb3ccb905cd0791c
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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