Pyridine → (Phenylmethoxy)carbamic acid 2,2,2-trichloroethyl ester

HRID 1290377Notes

Reaction equation

HRID 1290377 reaction equation
Cl.[CH2:2]([O:9][NH2:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]([Cl:25])([Cl:24])[Cl:23])=[O:19]>C(#N)C>[Cl:23][C:22]([Cl:25])([Cl:24])[CH2:21][O:20][C:18](=[O:19])[NH:10][O:9][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 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 of pyridine 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 0.5N 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. concentrationThe mixture is concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washThe organic layer is washed with 0.5N citric acid, water, saturated sodium bicarbonate, saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. distillationThe residue is purified by Kugelrohr distillation (bp 150° C. at 0.5 mmHg.)

Sources & evidence

ORD record
ord-b9704cb170654321b4b7c740c6fb56fa
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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