Potassium Carbonate → 4-(2-Chloroethoxy)benzamide
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 24 hours
- temperatureAfter cooling
- distillationdistilled water (2.0 l)
- additionwas added
- filtrationthe resultant precipitate filtered off
- washwashed with water
- customdried
- customCrystallisation from ethanol
Sources & evidence
- ORD record
- ord-ff08b8e42c454937acd7702212bbe622
- Source dataset
- uspto-grants-1992_01
- Patent number
- US05079248
Reaction notes
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