Chloroacetyl chloride → HCID 67597420, compound

HRID 582024Notes

Reaction equation

HRID 582024 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:9]=2)=[CH:4][CH:3]=1.[Cl:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)(Cl)Cl>[Cl:26][CH2:27][C:28]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=2)=[CH:4][CH:3]=1)=[O:29]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 543405974-(2,6-Diphenylpyridin-4-yl)aniline

Product 1

HCID 67597420HCID 67597420, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

50 ml of chloroform was added to 1.30 g of 4-(4-aminophenyl)-2,6-diphenylpyridine obtained in Reference Example 3, and a solution containing 0.32 ml of chloroacetyl chloride in 10 ml of chloroform was dropwise added thereto with stirring while ice cooling. Stirring was continued at room temperature for further one hour. The reaction solution was washed successively with an aqueous sodium bicarbonate saturated solutions, water and an aqueous sodium chloride saturated solution in this order and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residues were recrystallized from ethyl acetate-n-hexane, whereby 1.33 g of 2-chloro-N-[4-(2,6-diphenyl-4-pyridyl)phenyl]acetamide was obtained.

Workup

  1. customobtained in Reference Example 3
  2. additionwas dropwise added
  3. stirringStirring
  4. washThe reaction solution was washed successively with an aqueous sodium bicarbonate saturated solutions, water
  5. dry with materialan aqueous sodium chloride saturated solution in this order and dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residues were recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-387602752dd7435cade6e623578c7b4b
Source dataset
uspto-grants-1999_07
Patent number
US05922743

Reaction notes

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