4-Toluenesulfonyl chloride → HCID 178478104, compound

HRID 243520Notes

Reaction equation

HRID 243520 reaction equation
[OH-].[Na+].[NH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[NH:10][C:11]([NH:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:21])=S.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O.C1COCC1>[Cl:21][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]([Cl:20])[C:14]=1[N:13]=[C:11]1[NH:10][CH:5]2[CH2:6][CH2:7][CH2:8][CH2:9][CH:4]2[NH:3]1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 865952091-(2-Aminocyclohexyl)-3-(2,6-dichlorophenyl)thiourea

Product 1

HCID 178478104HCID 178478104, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium hydroxide (15.7 mg) and water (0.6 ml) was added under argon to a solution of 1-(2-aminocyclohexyl)-3-(2,6-dichlorophenyl)thiourea (50 mg) and THF (1.5 ml). Subsequently, a solution of p-toluenesulfonyl chloride (32.9 mg) and THF (0.5 ml) was added dropwise over fifteen minutes. After stirring for 60 minutes, the reaction mixture was added to water and extracted three times with ether. The combined organic phases were dried over magnesium sulfate, filtered and concentrated. 44 mg of the desired product were obtained.

Workup

  1. extractionextracted three times with ether
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-562ec7aa25de4138a5d2a44e9cac391b
Source dataset
uspto-grants-2014_02
Patent number
US08653259B2

Reaction notes

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