4-Toluenesulfonyl chloride → HCID 67599375, compound

HRID 1417322Notes

Reaction equation

HRID 1417322 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.[OH-].[Na+].[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>O.C(OCC)C>[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 67599363HCID 67599363, compound

Product 1

HCID 67599375HCID 67599375, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 3.4 g of 4-(4-aminobutoxy)benzonitrile hydrochloride (Example 52) is in 100 ml of water is treated successively with 3.5 ml of 10N NaOH and 3.5 g of 4-methylphenylsulfonyl chloride in 100 ml of diethyl ether. The mixture is stirred at room temperature for two hours, a precipitate forming. The solid is collected, washed with water and diethyl ether, dried, and recrystallized from 50% aqueous ethanol; m.p. 107°-108° C.; yield, 3.5 g.

Workup

  1. customa precipitate forming
  2. customThe solid is collected
  3. washwashed with water and diethyl ether
  4. customdried
  5. customrecrystallized from 50% aqueous ethanol
  6. customyield

Sources & evidence

ORD record
ord-38af011404904768a516f62e5f3cf206
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

Loading…