Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 19915736, compound

HRID 1089706Notes

Reaction equation

HRID 1089706 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].C1(C)C=CC(S(O[CH2:21][CH2:22][Cl:23])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:23][CH2:22][CH2:21][O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 3424033-Hydroxybenzamide

Product 1

HCID 19915736HCID 19915736, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of 3-hydroxybenzamide (21.6 g) in methyl ethyl ketone ("MEK") was added 2-chloroethyl p-toluenesulphonate (55.46 g) and potassium carbonate (16.0 g). After starting at reflux for 6 hours, the resultant mixture was poured onto water and a colourless solid filtered off. Crystallisation from ethanol gave the title compound, (22.2 g), m.p. 125°-126°.

Workup

  1. temperatureat reflux for 6 hours
  2. filtrationa colourless solid filtered off
  3. customCrystallisation from ethanol

Sources & evidence

ORD record
ord-472d978851664a56b66f705a7090d1d0
Source dataset
uspto-grants-1992_01
Patent number
US05079248

Reaction notes

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