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N-(2-Chloroethyl)-N-ethylaniline → 2-(N-ethylanilino)ethyl-(3-formamidopropyl)-dimethylazanium chloride

HRID 614728
Notes
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Reaction equation

HRID 614728 reaction equation
[CH3:1][N:2]([CH3:9])[CH2:3][CH2:4][CH2:5][NH:6][CH:7]=[O:8].[CH2:10]([N:12]([CH2:19][CH2:20][Cl:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11]>O>[Cl-:21].[CH3:1][N+:2]([CH3:9])([CH2:20][CH2:19][N:12]([CH2:10][CH3:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][CH2:4][CH2:5][NH:6][CH:7]=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7093N-(2-Chloroethyl)-N-ethylanilineHCID 80020N-(3-(dimethylamino)propyl)formamide

Product 1

HCID 211559472-(N-ethylanilino)ethyl-(3-formamidopropyl)-dimethylazanium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 157 parts of N-(3-dimethylaminopropyl)formamide in 20.0 parts of water was heated to 80° C. and over a period of one and one half hours there was added 171 parts of N-ethyl-N-(2-chloroethyl)aniline. The reaction mixture was heated at 95°-100° C. until a small sample when diluted with water gave a clear solution. After about seven hours of heating at 95°-100° C. there was obtained N,N-dimethyl-N-2-(N'-ethylanilino)ethyl-N-3-formamidopropylammonium chloride in the form of an aqueous solution.

Workup

  1. temperatureThe reaction mixture was heated at 95°-100° C. until a small sample when
  2. customgave a clear solution
  3. temperatureAfter about seven hours of heating at 95°-100° C.

Sources & evidence

ORD record
ord-125854c3f37c4bd8af03277e1278fd67
Source dataset
uspto-grants-1979_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04146558

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes