4-Toluenesulfonyl chloride → HCID 22139822, compound

HRID 2358192Notes

Reaction equation

HRID 2358192 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)(=O)=O)=CC=1>C1COCC1.O>[Cl:19][C:18]1[C:14]([NH:13][C:11]2[NH:10][C:3]3[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=3[N:1]=2)=[CH:15][S:16][CH:17]=1

Participants

6

Reactant 3

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

Product 1

HCID 22139822HCID 22139822, compoundYield 39.8%

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-efac69695db54118846a12cd3a5e779a
Source dataset
uspto-grants-2010_07
Patent number
US07763643B2

Reaction notes

Loading…