Dichloromethane → HCID 15714015, compound

HRID 1709267Notes

Reaction equation

HRID 1709267 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH3:25])[CH2:13][C:14]2[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20](O)=[O:21])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)[Cl:27]>O1CCCC1.S(Cl)(Cl)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH3:25])[CH2:13][C:14]2[CH:24]=[CH:23][C:17]([O:18][CH2:19][C:20]([Cl:27])=[O:21])=[CH:16][CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 14579384(4-{2-[(4-Chlorobenzene-1-sulfonyl)amino]propyl}phenoxy)acetic acid

Product 1

HCID 15714015HCID 15714015, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

1.15 g 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetic acid are dissolved in a mixture of 7 ml of methylene chloride and 7 ml of tetrahydrofuran, and 2.2 ml of thionyl chloride are added thereto. After the mixture is refluxed for 2 hours, the solvent is distilled off to give 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetyl chloride as ocherous oil. The product obtained above is dissolved in 10 ml of tetrahydrofuran. The solution and 6 ml of 0.6N an aqueous sodium hydroxide solution are added dropwise to a mixture of 787 mg of 6-aminohexanoic acid, 11 ml of 0.6N an aqueous sodium hydroxide solution, 20 ml of ethanol and 10 ml of ether under stirring at the same time. After the mixture is stirred at room temperature overnight, 50 ml of water and 50 ml of ether are added thereto. The aqueous layer is made acidic with 10% hydrochloric acid, extracted with ethyl acetate, washed, dried, filtered, and evaporated to remove the solvent. Thus obtained pale yellow caramel is purified by silica gel column chromatography (solvent; chloroform, then chloroform: methanol=9:1) to give 1.50 g of 6-{ 4-[2-(4-chlorophenyl)sulfonylaminopropyl]phenoxyacetylamino}-n-hexanoic acid as colorless oil.

Workup

  1. additionare added
  2. temperatureAfter the mixture is refluxed for 2 hours
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-7ee3d2bf10444a56a415348b22a9257a
Source dataset
uspto-grants-1990_08
Patent number
US04948810

Reaction notes

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