4-Toluenesulfonyl chloride → HCID 178420482, compound

HRID 243518Notes

Reaction equation

HRID 243518 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=S.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CCOCC.O.C1COCC1>[O:3]1[CH2:4][CH2:5][CH2:6][NH:7][C:8]1=[N:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 2063437HCID 2063437, compound

Product 1

HCID 178420482HCID 178420482, compoundYield 65.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium hydroxide (23.8 mg) and water (0.6 ml) was added under argon and with stirring to a solution of 1-(3-hydroxypropyl)-3-phenylthiourea (50 mg) and THF (1.5 ml). Subsequently, a solution of p-toluenesulfonyl chloride (49.9 mg) and THF (0.5 ml) was added dropwise over fifteen minutes. After stirring for 30 minutes, the reaction mixture was added to water, and extraction was effected three times with ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. Chromatography using silica gel (initially 50:1 methylene chloride/methanol, at the end 100:1 methanol/saturated ammonia solution) afforded 27.4 mg of the desired product.

Workup

  1. dry with materialThe combined organic phases were dried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-32102401fb344964a48934448ec33d1d
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Reaction notes

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