Potassium Carbonate → 4-(2-Chloroethoxy)benzamide

HRID 1089711Notes

Reaction equation

HRID 1089711 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, 1.25 M), 2-(benzenesulphonyloxy)ethyl chloride (359 g, 1.8 M), and potassium carbonate (172.8 g, 1.25 M) in butan-2-one (2.16 l) was stirred at reflux for 24 hours. After cooling, distilled water (2.0 l) 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 l)
  4. additionwas added
  5. filtrationthe resultant precipitate filtered off
  6. washwashed with water
  7. customdried
  8. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-ff08b8e42c454937acd7702212bbe622
Source dataset
uspto-grants-1992_01
Patent number
US05079248

Reaction notes

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