Water → HCID 18520204, compound

HRID 1368268Notes

Reaction equation

HRID 1368268 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]1(C)[C:17]([SH:18])=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20]([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:14]1([CH3:20])[CH:13]=[CH:12][C:17]([S:18][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH2:11])(=[O:10])=[O:9])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 87122-ThiocresolHCID 11430Potassium CarbonateHCID 814102-Chlorobenzenesulfonamide

Product 1

HCID 18520204HCID 18520204, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.0 g of 2-chlorobenzenesulfonamide, 2.0 g of thiocresol and 6.5 g of K2CO3 are stirred at 100° C. for 6 h in 30 ml of DMF and then at 120° C. for 13 h. The reaction mixture is poured onto 200 ml of water and extracted with 500 ml of EA. The organic phase is then washed with 100 ml of a saturated aqueous Na2CO3 solution. It is dried over MgSO4 and the solvent is removed in vacuo. Chromatography on silica gel using DIP yields 1.4 g of white crystals, m.p. 122-124° C.

Workup

  1. extractionextracted with 500 ml of EA
  2. washThe organic phase is then washed with 100 ml of a saturated aqueous Na2CO3 solution
  3. dry with materialIt is dried over MgSO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-802402efd00544cd8a1bb5ea528c3e2e
Source dataset
uspto-grants-2003_06
Patent number
US06573288B1

Reaction notes

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