Chloroacetyl chloride → HCID 20574934, compound

HRID 894268Notes

Reaction equation

HRID 894268 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][CH2:8][CH2:9][N:10]=[C:11]1[CH:16]([CH3:17])[CH2:15][CH2:14][CH2:13][CH:12]1[CH3:18].C(N(CC)CC)C>CCCCCC>[CH3:18][C:12]1[CH2:13][CH2:14][CH2:15][CH:16]([CH3:17])[C:11]=1[N:10]([CH2:9][CH2:8][O:7][CH3:6])[C:3](=[O:4])[CH2:2][Cl:1]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 20574933HCID 20574933, compound

Product 1

HCID 20574934HCID 20574934, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Over a period of 3 hours and at 20°-30° C. 37.5 g of chloroacetylchloride are added dropwise while stirring to a solution of 57 g of N-(2-methoxy-ethyl)-2,6-dimethylcyclohexylideneamine in 200 ml of hexane. Afterwards during 2 hours 48 ml of triethylamine are added dropwise in the course of which the temperature of the mixture rises to ca. 50° C. Subsequently the mixture is heated under reflux for 30 minutes and poured onto ice. The organic layer is washed with water and dried over sodium sulfate. The solvent is distilled off and the residue is fractionally distilled: 54.5 g of N-(2,6-dimethyl-1-cyclohexene-1-yl)-N-(2-methoxyethyl)-α-chloro-acetamide are obtained, b.p. 136°-139° C./0.1 Torr.

Workup

  1. customat 20°-30° C
  2. customrises to ca. 50° C
  3. temperatureSubsequently the mixture is heated
  4. temperatureunder reflux for 30 minutes
  5. additionpoured onto ice
  6. washThe organic layer is washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationThe solvent is distilled off
  9. distillationthe residue is fractionally distilled

Sources & evidence

ORD record
ord-d8ed075bbfc84b1594185272368d8328
Source dataset
uspto-grants-1981_08
Patent number
US04283221

Reaction notes

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