Triethylamine → 4-Chlorobenzenesulfonamide

HRID 1492544Notes

Reaction equation

HRID 1492544 reaction equation
OC1C=CC(C(CC2C=NC=CC=2)C[NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])=CC=1.C(N(CC)CC)C.C(Cl)(=O)OCC>O1CCCC1>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([S:11]([NH2:10])(=[O:12])=[O:13])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 18950677HCID 18950677, compound

Product 1

HCID 668244-Chlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A portion of 53 mg of N-[2-(4-hydroxyphenyl)-3-(3-pyridyl)propyl]-4-chlorobenzenesulfonamide and 78 mg of triethylamine were dissolved in 8 ml of tetrahydrofuran, followed by addition of 25 mg of ethyl chlorocarbonate dissolved in 1 ml of tetrahydrofuran, and stirred at room temperature for 10 minutes. The crystalline deposited was filtered, and the filtrate was then concentrated under reduced pressure. The residue was subjected to chromatography on a silica gel column, and from a fraction eluted with methanol-methylene chloride (5:95 v/v) was obtained 53 mg of N-[2-(4-ethoxycarbonyloxyphenyl)-3-(3-pyridyl)}propyl]-4-chlorobenzenesulfonamide. The spectrometric data supports the structure of [32] as follows.

Workup

  1. filtrationThe crystalline deposited was filtered
  2. concentrationthe filtrate was then concentrated under reduced pressure
  3. washfrom a fraction eluted with methanol-methylene chloride (5:95 v/v)

Sources & evidence

ORD record
ord-79ee0d75002f4f1faea4c11dec357b22
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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