2,5-Dichloroaniline → HCID 21396418, compound

HRID 1439760Notes

Reaction equation

HRID 1439760 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[CH2:10]([N:12]([CH2:15][CH2:16]Cl)[CH2:13][CH3:14])[CH3:11].Cl[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].C(COC)OC>C(N(CC)CC)C>[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[N:4]([CH2:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21])[CH2:11][CH2:10][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 72622,5-DichloroanilineHCID 80711,2-DimethoxyethaneHCID 107572-ChloroacetophenoneHCID 13364Diethylaminoethyl chloride

Product 1

HCID 21396418HCID 21396418, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of 0.05 mole of N-(2,5-dichlorophenyl)-N',N'-diethylethylenediamine obtained by alkylating 2,5-dichloroaniline with N,N-diethyl-β-chloroethylamine, and 0.05 mole of 2-chloroacetophenone in dimethoxyethane containing 0.05 mole of triethylamine was stirred at room temperature for 24 hours under a nitrogen atmosphere after which the solvent was removed at reduced pressure. The residue was dissolved in 200 ml of chloroform and washed with 5% aqueous sodium carbonate, dried over sodium sulfate and evaporated to dryness to give 2-[N-(2,5-dichlorophenyl)-N-(β-diethylaminoethyl)amino]acetophenone.

Workup

  1. customwas removed at reduced pressure
  2. dissolutionThe residue was dissolved in 200 ml of chloroform
  3. washwashed with 5% aqueous sodium carbonate
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-9adc9474018b4fcb9e05000813ce69ce
Source dataset
uspto-grants-1977_11
Patent number
US04060630

Reaction notes

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