4-Toluenesulfonyl chloride → HCID 67598288, compound

HRID 1417327Notes

Reaction equation

HRID 1417327 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>ClCCl>[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][S:11][C:8]2[CH:9]=[CH:10][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[CH:6][CH:7]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 28280956HCID 28280956, compound

Product 1

HCID 67598288HCID 67598288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7.2 g of 4-[4-(acetamido)phenylthio]butaneamine (Example 70) in 100 ml of dichloromethane containing 8 ml of triethylamine is added 6.2 g of 4-methylbenzenesulfonyl chloride. The mixture is then stirred under reflux for six hours. The solvents are removed in vacuo. The residue is triturated with 2 portions of 100 ml of water. The insoluble portion is recrystallized from aqueous ethanol. Initially, the product precipitates as an oil, but after standing, crystals are obtained, m.p. 104°-105° C.; yield, 6.6 g.

Workup

  1. temperatureunder reflux for six hours
  2. customThe solvents are removed in vacuo
  3. customThe residue is triturated with 2 portions of 100 ml of water
  4. customThe insoluble portion is recrystallized from aqueous ethanol
  5. customInitially, the product precipitates as an oil
  6. customcrystals are obtained
  7. customyield

Sources & evidence

ORD record
ord-ecfb0d0193bc4c5da2137747352ff7cc
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

Loading…