Chloroacetyl chloride → HCID 54339889, compound

HRID 2072203Notes

Reaction equation

HRID 2072203 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]=[N:16][CH:17]([NH2:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:30][CH2:31][C:32](Cl)=[O:33]>C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]=[N:16][CH:17]([NH:23][C:32](=[O:33])[CH2:31][Cl:30])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 85923562HCID 85923562, compound

Product 1

HCID 54339889HCID 54339889, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 12.5 g. of ethyl [2-(2-pyridinecarbonyl)phenyl]azo-aminoacetate in 400 ml. of anhydrous benzene are added 11.4 g. of potassium carbonate and 8.0 ml. of chloroacetyl chloride. The resulting mixture is refluxed with stirring for 30 minutes, and then cooled. The resulting precipitate is collected by filtration, and partitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform. The chloroform layer is separated, washed with water, dried over sodium sulfate, followed by evaporation of the solvent to give ethyl [2-(2-pyridinecarbonyl)phenyl]azo-(2-chloroacetamido)-acetate as crystals. Recrystallization from acetone-n-hexane gives yellow needles, melting at 160 to 162° C.

Workup

  1. temperatureThe resulting mixture is refluxed
  2. temperaturecooled
  3. filtrationThe resulting precipitate is collected by filtration
  4. custompartitioned between saturated aqueous sodium hydrogen carbonate solution and chloroform
  5. customThe chloroform layer is separated
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-98ec3981a0f743e38aef282915f4065e
Source dataset
uspto-grants-1977_09
Patent number
US04049812

Reaction notes

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