Chloroacetyl chloride → 11-[(2-chloroacetyl)amino]undecanoic acid

HRID 973249Notes

Reaction equation

HRID 973249 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[Cl:15][CH2:16][C:17](Cl)=[O:18]>C(OCC)(=O)C>[Cl:15][CH2:16][C:17]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[O:18]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 1708311-Aminoundecanoic acid

Product 1

HCID 31536111-[(2-chloroacetyl)amino]undecanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

11-Aminoundecanoic acid (10.7 grams; 0.05 mole) was added to 125 ml of ethyl acetate and refluxed with 5 ml of chloroacetyl chloride as above. After one hour no precipitate was noted and the excess chloroacetyl chloride and ethyl acetate was removed by vacuum distillation. 14 Grams (96% yield) of N-chloroacetylamino-11-undecanoic acid was obtained. This compound was confirmed by elemental analysis and infrared spectroscopy.

Workup

  1. customthe excess chloroacetyl chloride and ethyl acetate was removed by vacuum distillation

Sources & evidence

ORD record
ord-dfc2044f77d94a679c3a98792581ed1c
Source dataset
uspto-grants-1977_10
Patent number
US04055663

Reaction notes

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