Chloroacetyl chloride → HCID 21410921, compound

HRID 2072206Notes

Reaction equation

HRID 2072206 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]([NH2:21])[C:18]([NH2:20])=[O:19])=[O:8].C(=O)([O-])[O-].[K+].[K+].[Cl:28][CH2:29][C:30](Cl)=[O:31]>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:21][C:30](=[O:31])[CH2:29][Cl:28])[C:18]([NH2:20])=[O:19])=[O:8]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 21410948HCID 21410948, compound

Product 1

HCID 21410921HCID 21410921, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 0.85 g. of [2-(2-pyridinecarbonyl)-phenyl]azo-aminoacetamide in 30 ml. of anhydrous benzene are added 0.42 g. of potassium carbonate and 1.0 ml. of chloroacetyl chloride. The mixture is refluxed with stirring for 45 minutes, and then cooled. The precipitated crystals are 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, and then the solvent is removed by distillation to give [2-(2-pyridinecarbonyl)phenyl]azo-(2-chloroacetamido)acetamide as crystals. Recrystallization from ethanol gives yellow needles, melting at 204° to 205° C. (decomposition).

Workup

  1. temperatureThe mixture is refluxed
  2. temperaturecooled
  3. filtrationThe precipitated crystals are 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. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-6f88a701bf644d84b225ff9e6f110f6e
Source dataset
uspto-grants-1977_09
Patent number
US04049812

Reaction notes

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