4-Toluenesulfonyl chloride → HCID 178478945, compound

HRID 1724682Notes

Reaction equation

HRID 1724682 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:30])(=O)=O)=CC=1.C(OCC)(=O)C>C1COCC1.O>[ClH:18].[Cl:30][C:14]1[S:15][CH:16]=[C:17]([Cl:18])[C:13]=1[NH:12][C:10]1[NH:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[N:1]=1

Participants

7

Reactant 4

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

Product 1

HCID 178478945HCID 178478945, compoundYield 38.5%

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-1bdb5ac727d44f4ea2c2ddcf6c84fa3f
Source dataset
uspto-grants-2009_02
Patent number
US07488746B2

Reaction notes

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