Dimethylformamide → 2-acetylamino-4-nitrophenyl beta-N,N-diethylaminoethyl ether

HRID 1065590Notes

Reaction equation

HRID 1065590 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:6]=1[OH:14])(=[O:3])[CH3:2].[K].CN(C)C=O.[CH2:21]([N:23]([CH2:26][CH2:27]Cl)[CH2:24][CH3:25])[CH3:22]>O>[CH2:21]([N:23]([CH2:26][CH2:27][O:14][C:6]1[CH:7]=[CH:8][C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[NH:4][C:1](=[O:3])[CH3:2])[CH2:24][CH3:25])[CH3:22]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 13364Diethylaminoethyl chlorideHCID 3292867Acetamide, N-(2-hydroxy-5-nitrophenyl)-HCID 5462222Potassium

Product 1

HCID 154510202-acetylamino-4-nitrophenyl beta-N,N-diethylaminoethyl ether

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

117 g (0.5 mol) of 2-acetylamino-4-nitrophenol, in the form of the potassium salt, are introduced into 350 ml of dimethylformamide and the mixture is then heated to 60° C., whilst stirring. 88.2 g (0.65 mol) of diethylaminoethyl chloride are then added; the reaction medium is heated at 95° C. for 150 minutes and is then poured into 1,500 ml of iced water; the expected product precipitates. This product is filtered off and washed with a 0.5 N sodium carbonate solution and then with water. After filtration, the product is finally dried in vacuo at 45° C. It melts at 117° C.

Workup

  1. temperaturethe reaction medium is heated at 95° C. for 150 minutes
  2. customthe expected product precipitates
  3. filtrationThis product is filtered off
  4. washwashed with a 0.5 N sodium carbonate solution
  5. filtrationAfter filtration
  6. customthe product is finally dried in vacuo at 45° C

Sources & evidence

ORD record
ord-b03664e732954654baa65f4cd93fe1e4
Source dataset
uspto-grants-1982_05
Patent number
US04330292

Reaction notes

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