Potassium Carbonate → 4-(2-Chloroethoxy)benzamide

HRID 1032681Notes

Reaction equation

HRID 1032681 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C1(S(O[CH2:21][CH2:22][Cl:23])(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[Cl:23][CH2:22][CH2:21][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 136344852-Chloroethyl Benzenesulfonate

Product 1

HCID 135691714-(2-Chloroethoxy)benzamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxybenzamide (194 g, 1.25M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8M), and potassium carbonate (172.8 g, 1.25M) in butan-2-one (2.16 1) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 1) was added and the resultant precipitate filtered off, washed with water, and dried. Crystallisation from ethanol gave the title compound, yield (232.0 g), m.p. 66°.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureAfter cooling
  3. distillationdistilled water (2.0 1)
  4. additionwas added
  5. filtrationthe resultant precipitate filtered off
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-5a6182fcaddf40e0a3bba976ba19cbe9
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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