Chloroacetyl chloride → HCID 13132292, compound

HRID 621163Notes

Reaction equation

HRID 621163 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:22])[CH2:11][NH:12][CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:29][CH2:30][C:31](Cl)=[O:32]>C(OCC)(=O)C>[CH2:2]([O:9][C:10](=[O:22])[CH2:11][N:12]([C:31](=[O:32])[CH2:30][Cl:29])[CH:13]1[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 13089233HCID 13089233, compound

Product 1

HCID 13132292HCID 13132292, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-(Indan-2-yl)glycine benzyl ester hydrochloride (6 g) is added to a mixture of 300 ml of ethyl acetate and 200 ml of 5% aqueous potassium carbonate, followed by vigorous stirring. To the resulting solution is added dropwise 6 ml of chloroacetyl chloride over 30 minutes with ice cooling. Thereafter, stirring is continued for an hour. The ethyl acetate layer is then separated, washed with water and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Addition of ether to the residue gives 6 g of N-chloroacetyl-N-(indan-2-yl)glycine benzyl ester as colorless scales melting at 99.5°-100.5° C.

Workup

  1. waitis continued for an hour
  2. customThe ethyl acetate layer is then separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. additionAddition of ether to the residue

Sources & evidence

ORD record
ord-8cb63f3ec47549539d8dd14c1bd0e761
Source dataset
uspto-grants-1989_04
Patent number
US04822818

Reaction notes

Loading…