Diisopropylamine → Phenyl 4-fluoro-2-nitrophenylcarbamate

HRID 1901058Notes

Reaction equation

HRID 1901058 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(NC(C)C)(C)C.Cl[C:20]([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>ClCCl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20](=[O:21])[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 15891Phenyl chloroformateHCID 677694-Fluoro-2-nitroaniline

Product 1

HCID 23370075Phenyl 4-fluoro-2-nitrophenylcarbamateYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-fluoro-2-nitroaniline (1.56 g) and diisopropylamine (1.68 ml) in dichloromethane (20 ml) was added dropwise under ice-cooling phenyl chloroformate (1.51 g). After stirring the mixture at room temperature overnight, the reaction solution was washed with water, saturated saline, dried over anhydrous MgSO4 and the solvent was distilled off. Crystallization of the residue from diisopropyl ether afforded phenyl 4-fluoro-2-nitrophenylcarbamate (0.79 g, 29%) as crystals.

Workup

  1. washthe reaction solution was washed with water, saturated saline
  2. dry with materialdried over anhydrous MgSO4
  3. distillationthe solvent was distilled off
  4. customCrystallization of the residue from diisopropyl ether

Sources & evidence

ORD record
ord-4bb9718890f247318728fbcea8bc5ab7
Source dataset
uspto-grants-1996_11
Patent number
US05576335

Reaction notes

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