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

HRID 462153Notes

Reaction equation

HRID 462153 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 cloride. The mixture is stirred at room temperature for 16 l hours and then at 60°-65° C. for 2 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. customInsoluble material is removed by filtration
  2. temperaturethe resulting solution is heated at the boil for two hours
  3. customsuch in the preparation of dyes

Sources & evidence

ORD record
ord-fcbd66149d40432b977da38e3ff60b83
Source dataset
uspto-grants-1977_12
Patent number
US04065500

Reaction notes

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