Water → ethyl N-(2-fluorophenyl)carbamate

HRID 2372208Notes

Reaction equation

HRID 2372208 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].Cl[C:10]([O:12][CH2:13][CH3:14])=[O:11].[OH-].[Na+].O>CCOCC>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:10](=[O:11])[O:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 95842-FluoroanilineHCID 10928Ethyl chloroformate2×HCID 14798Sodium Hydroxide

Product 1

HCID 242730ethyl N-(2-fluorophenyl)carbamate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-fluoroaniline (11.1 g, 100.0 mmol) in 100 ml of dry ether cooled in an ice bath is added ethyl chloroformate (7.1 ml, 8.1 g, 75.0 mmol). After addition, the mixture is allowed to warm to RT and is stirred at RT for 3 hours. Then a 10% sodium hydroxide solution (54 ml, 2.8M, 150.0 mmol) is added, followed by another 7.1 ml of ethyl chloroformate. The mixture is stirred at RT for 3 hours, and is then poured into water and ether. The organic layer is separated, washed with 5% HCl and with brine, and dried. The solvent is removed to give ethyl N-(2-fluorophenyl)carbamate.

Workup

  1. additionAfter addition
  2. stirringThe mixture is stirred at RT for 3 hours
  3. customThe organic layer is separated
  4. washwashed with 5% HCl and with brine
  5. customdried
  6. customThe solvent is removed

Sources & evidence

ORD record
ord-35b1058271fe4787be2346219ff142a1
Source dataset
uspto-grants-1992_03
Patent number
US05098466

Reaction notes

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