4-Toluenesulfonyl chloride → HCID 178505472, compound

HRID 2250509Notes

Reaction equation

HRID 2250509 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:17]([Cl:18])=[CH:16][S:15][CH:14]=1)=S.[OH-].[Na+].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(OCC)(=O)C>C1COCC1.O>[Cl:18][C:17]1[C:13]([NH:12][C:10]2[NH:9][C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[N:1]=2)=[CH:14][S:15][CH:16]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22139853HCID 22139853, compound

Product 1

HCID 178505472HCID 178505472, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-Amino-4-fluoro-phenyl)-3-(4-chloro-thiophen-3-yl)-thiourea (625 mg) was dissolved in THF and a solution of NaOH (0,207 g) in water (9 ml) was added. Within 5 min a solution of p-toluenesulfonyl chloride (0,395 g) in THF (10 ml) was added dropwise. After stirring for one hour at room temperature water and ethyl acetate were added to the reaction mixture. The organic layer was separated and the aqueous phase was extracted three times with ethyl acetate. The combined organic layers were dried (MgSO4), treated with charcoal, filtered and the solvent evaporated to yield the desired product (135 mg).

Workup

  1. additionwere added to the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-75038674fd8d489b82bf543e95cdfdbc
Source dataset
uspto-grants-2008_01
Patent number
US07317033B2

Reaction notes

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