Potassium Carbonate → 2-(2-Chloroethoxy)benzene-1-sulfonamide

HRID 1981251Notes

Reaction equation

HRID 1981251 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC(C(S(O[CH2:30][CH2:31][Cl:32])(=O)=O)=O)=CC=1>C(C(C)=O)C>[Cl:32][CH2:31][CH2:30][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6375462-Hydroxybenzene-1-sulfonamideHCID 539698672-Chloroethyl p-toloylsulfonate

Product 1

HCID 137294542-(2-Chloroethoxy)benzene-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 9.0 g of 2-hydroxyphenylsulfonamide, 7.9 g of potassium carbonate, 13.3 g of 2-chloroethyl p-toloylsulfonate and 80 ml of ethylmethylketone is refluxed for 40 hours. The reaction mixture is cooled to room temperature, filtrated and evaporated to dryness. From the oily residue crystallise after addition of a small portion of methylene chloride 7.0 g of 2-(2-chloroethoxy)-phenylsulfonamide, m.p. 110° C.

Workup

  1. temperatureis refluxed for 40 hours
  2. filtrationfiltrated
  3. customevaporated to dryness
  4. customFrom the oily residue crystallise
  5. additionafter addition of a small portion of methylene chloride 7.0 g of 2-(2-chloroethoxy)-phenylsulfonamide, m.p. 110° C.

Sources & evidence

ORD record
ord-2dd14a13353a49bf95478b95afaa1780
Source dataset
uspto-grants-1985_04
Patent number
US04514212

Reaction notes

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