4'-Chloroacetyl(acetanilide) → N,N-Dimethyl-N-(p-aminophenacyl)-N-3-aminopropylammonium chloride

HRID 614726Notes

Reaction equation

HRID 614726 reaction equation
[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][CH2:5][NH:6]C=O.C([NH:13][C:14]1[CH:23]=[CH:22][C:17]([C:18](=[O:21])[CH2:19][Cl:20])=[CH:16][CH:15]=1)(=O)C>O>[Cl-:20].[CH3:1][N+:2]([CH3:9])([CH2:19][C:18]([C:17]1[CH:16]=[CH:15][C:14]([NH2:13])=[CH:23][CH:22]=1)=[O:21])[CH2:3][CH2:4][CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 88054'-Chloroacetyl(acetanilide)HCID 80020N-(3-(dimethylamino)propyl)formamide

Product 1

HCID 86735871N,N-Dimethyl-N-(p-aminophenacyl)-N-3-aminopropylammonium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 143.5 parts of N-(3-dimethylaminopropyl)formamide and 700 parts of water is added 249 parts of p-acetamidophenacyl chloride. The mixture is stirred at room temperature for 16 hours and then at 60°-65° C. for two hours. Insoluble material is removed by filtration. The filtrate is combined with one-half its volume of concentrated hydrochloric acid (36% by weight) and the resulting solution is heated at the boil for two hours. The aqueous solution of N,N-dimethyl-N-(p-aminophenacyl)-N-3-aminopropylammonium chloride is used as such in the preparation of dyes.

Workup

  1. waitat 60°-65° C. for two hours
  2. customInsoluble material is removed by filtration
  3. temperaturethe resulting solution is heated at the boil for two hours
  4. customsuch in the preparation of dyes

Sources & evidence

ORD record
ord-2c9f4c4e4e694eb18fe1071a04bb37b3
Source dataset
uspto-grants-1979_03
Patent number
US04146558

Reaction notes

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