Water → HCID 54410400, compound

HRID 597695Notes

Reaction equation

HRID 597695 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].[OH:10][N:11]=[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:13]#[N:14].C(N(CC)CC)C.O>C1C=CC=CC=1>[Cl:7][C:6]([Cl:9])([Cl:8])[CH2:5][O:4][C:2]([O:10][N:11]=[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:13]#[N:14])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 699982-(Hydroxyimino)-2-phenylacetonitrileHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 54410400HCID 54410400, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 2,2,2-trichloroethyl chloroformate (2.2 g.) in benzene (10 ml.) was added dropwise to a solution of 2-hydroxyimino-2-phenylacetonitrile (1.5 g.) and triethylamine (1.40 ml.) in benzene (20 ml.) at room temperature, the mixture was stirred for 3 hours at the same temperature. Benzene and water were added to the reaction mixture layer was washed with water and dried over magnesium sulfate. The solvent was distilled off and the residue was crystallized by adding a small amount of ether and n-hexane. The crystals were collected by filtration and recrystallized from methanol to give 2-(2,2,2-trichloroethoxycarbonyloxyimino)-2-phenylacetonitrile (2.7 g.), mp 82° to 84° C.

Workup

  1. washwas washed with water
  2. dry with materialdried over magnesium sulfate
  3. distillationThe solvent was distilled off
  4. customthe residue was crystallized
  5. additionby adding a small amount of ether and n-hexane
  6. filtrationThe crystals were collected by filtration
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a33c05d8b80d4483a617aebac436d385
Source dataset
uspto-grants-1977_03
Patent number
US04014915

Reaction notes

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