Chloroacetyl chloride → HCID 20543895, compound

HRID 2285646Notes

Reaction equation

HRID 2285646 reaction equation
[CH2:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH3:9])[C:4]1=[N:10][CH:11]([CH3:15])[CH2:12][O:13][CH3:14])[CH3:2].C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C1C=CC=CC=1>[Cl:23][CH2:24][C:25]([N:10]([CH:11]([CH3:15])[CH2:12][O:13][CH3:14])[C:4]1[CH:5]([CH3:9])[CH2:6][CH2:7][CH2:8][C:3]=1[CH2:1][CH3:2])=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 20543892HCID 20543892, compound

Product 1

HCID 20543895HCID 20543895, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

174 g (0.83 mole) of 2-ethyl-6-methyl-N-(1-methyl-2-methoxyethyl)-cyclohexylideneamine and 101 g (1 mole) of triethylamine were added dropwise one after the other with stirring and at a temperature of 5° C. to a solution of 94 g (0.83 mole) of chloroacetyl chloride in 3000 ml of benzene. The reaction mixture was then refluxed for 5 hours, cooled to room temperature, washed with water, dried with sodium sulfate, filtered and concentrated under water-jet vacuum. Distillation of the residue under high vacuum gave 150,5 g of a 2-chloro-N-(1-methyl-2-methoxy-ethyl)-N-(2-ethyl-6-methyl-cyclohexenyl)acetamide as a mixture of its isomers b.p. 140°-148°/0.1 Torr.

Workup

  1. temperatureThe reaction mixture was then refluxed for 5 hours
  2. washwashed with water
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under water-jet vacuum
  6. distillationDistillation of the residue under high vacuum

Sources & evidence

ORD record
ord-22048a2c184d4871bd3ebeef51157992
Source dataset
uspto-grants-1982_04
Patent number
US04324580

Reaction notes

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