2,2,2-Trichloroethyl chloroformate → (Phenylmethoxy)carbamic acid 2,2,2-trichloroethyl ester

HRID 1600105Notes

Reaction equation

HRID 1600105 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:12]([O:14][CH2:15][C:16]([Cl:19])([Cl:18])[Cl:17])=[O:13]>C(#N)C>[Cl:17][C:16]([Cl:19])([Cl:18])[CH2:15][O:14][C:12](=[O:13])[NH:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 102312Benzyloxyamine hydrochloride

Product 1

HCID 11098567(Phenylmethoxy)carbamic acid 2,2,2-trichloroethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Under anhydrous conditions, 50 g of O-benzylhydroxylamine hydrochloride is suspended in 783 ml of acetonitrile. To the suspension is added 50.6 ml ofpyridine followed by dropwise addition of 43.15 ml trichloroethyl chloroformate in 235 ml of acetonitrile. The reaction is allowed to stir overnight at room temperature. The mixture is concentrated in vacuo and diluted with ethyl acetate. The organic layer is washed with 0.5M citric acid, water, saturated sodium bicarbonate, saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by Kugelrohr distillation (bp 150° C. at 0.5 mmHg.) to give 70 g of the desired product.

Workup

  1. additionTo the suspension is added 50.6 ml ofpyridine
  2. concentrationThe mixture is concentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. washThe organic layer is washed with 0.5M citric acid, water, saturated sodium bicarbonate, saturated sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo
  7. distillationThe residue is purified by Kugelrohr distillation (bp 150° C. at 0.5 mmHg.)

Sources & evidence

ORD record
ord-3ac898b34da74a709d4cfc4832d96d2d
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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