4-Toluenesulfonyl chloride → HCID 22139857, compound

HRID 1724684Notes

Reaction equation

HRID 1724684 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[NH:10][C:11]([NH:13][C:14]1[C:18]([Cl:19])=[CH:17][S:16][CH:15]=1)=S.[OH-].[Na+].C1(C)C=CC(S([Cl:31])(=O)=O)=CC=1>C1COCC1.O>[ClH:19].[Cl:31][C:15]1[S:16][CH:17]=[C:18]([Cl:19])[C:14]=1[NH:13][C:11]1[NH:10][C:3]2[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 22139821HCID 22139821, compound

Product 1

HCID 22139857HCID 22139857, compoundYield 63.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 1-(2-amino-4,5-difluoro-phenyl)-3-(4-chloro-thiophen-3-yl)-thiourea (773 mg) in THF (20 ml) a solution of NaOH (240 mg) in water (9 ml) was added followed by a solution of p-toluenesulfonyl chloride (528 mg) in THF (10 ml). Following the analogous description in example 54b) the desired product (275 mg) was obtained.

Sources & evidence

ORD record
ord-e300e6c45dee46828b346d44a30360df
Source dataset
uspto-grants-2009_02
Patent number
US07488746B2

Reaction notes

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