Acetic Acid → HCID 19424353, compound

HRID 743135Notes

Reaction equation

HRID 743135 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[O:20])[CH3:19].C(O)(=O)C.[C-:25]#[N:26].[K+]>O>[C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][CH:4]([C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])[C:25]#[N:26])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 67372,6-DichlorobenzaldehydeHCID 9032Potassium CyanideHCID 110862'-Aminoacetophenone

Product 1

HCID 19424353HCID 19424353, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.75 parts of 2,6-dichlorobenzaldehyde, 5.4 parts of 1-(2-aminophenyl)-1-ethanone and 105 parts of acetic acid was stirred for 1/2 hour at room temperature. There were added 3.26 parts of potassium cyanide and stirring was continued for 20 hours. The reaction mixture was diluted with water. The precipitate was filtered off, washed with water and recrystallized from acetonitrile. The product was filtered off and dried, yielding 9.1 parts (71.3%) of (±)-α-[(2-acetylphenyl)amino]-2,6-dichlorobenzeneacetonitrile; mp. 178.7° C. (interm. 3).

Workup

  1. stirringstirring
  2. waitwas continued for 20 hours
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customrecrystallized from acetonitrile
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-6a58604867634292b2fc2a8edf4e3e51
Source dataset
uspto-grants-1996_09
Patent number
US05556886

Reaction notes

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