2,2,2-Trichloroethyl chloroformate → N-(beta,beta,beta-trichloroethoxycarbonyl)-3-pyrroline

HRID 971676Notes

Reaction equation

HRID 971676 reaction equation
C([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)C1C=CC=CC=1.Cl[C:14]([O:16][CH2:17][C:18]([Cl:21])([Cl:20])[Cl:19])=[O:15]>C1C=CC=CC=1>[Cl:19][C:18]([Cl:21])([Cl:20])[CH2:17][O:16][C:14]([N:8]1[CH2:12][CH:11]=[CH:10][CH2:9]1)=[O:15]

Participants

4

Reactant 2

HCID 870632,2,2-Trichloroethyl chloroformateHCID 5615061-Benzyl-2,5-dihydropyrrole

Product 1

HCID 13192204N-(beta,beta,beta-trichloroethoxycarbonyl)-3-pyrroline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

40.0 g (0.25 mol) of N-benzyl-3-pyrroline are dissolved in 400 ml of benzene. 53.0 g (0.25 mol) of 2,2,2-trichloroethyl chloroformate are introduced into this solution in the course of 30 minutes, at 0° and under a nitrogen atmosphere. The reaction mixture is stirred for a further 1 hour at 0°, then washed at room temperature twice with, in each case, 100 ml of a mixture of water and 2 N hydrochloric acid (3:1) and then twice with water, dried over sodium sulphate and evaporated under a water pump vacuum. The oily residue is distilled under a high vacuum and, after 24 g of benzyl chloride has been separated off, N-(β,β,β-trichloroethoxycarbonyl)-3-pyrroline with a boiling point of 84°-85° C./0.12 mm Hg is obtained.

Workup

  1. washwashed at room temperature twice with, in each case, 100 ml of a mixture of water and 2 N hydrochloric acid (3:1)
  2. dry with materialtwice with water, dried over sodium sulphate
  3. customevaporated under a water pump vacuum
  4. distillationThe oily residue is distilled under a high vacuum
  5. customafter 24 g of benzyl chloride has been separated off

Sources & evidence

ORD record
ord-726ffd3177344721ba902f780bc0581c
Source dataset
uspto-grants-1979_07
Patent number
US04160837

Reaction notes

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