m-Chloroperbenzoic acid → HCID 67745317, compound

HRID 375484Notes

Reaction equation

HRID 375484 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]1([C:18]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:23]=[CH:22][S:21](=[O:24])[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl>[C:12]1([C:18]2([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:19]=[CH:20][S:21](=[O:6])(=[O:24])[CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 67745332HCID 67745332, compound

Product 1

HCID 67745317HCID 67745317, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 1.12 g of 3-chloroperoxybenzoic acid (at 85%) in 25 cm3 of dry dichloromethane is added to a solution of 1.47 g of 3,4-dihydro-4,4-diphenyl-2H-thiapyran 1-oxide in 15 cm3 of dry dichloromethane. After stirring for 20 hours at 20° C. the reaction mixture is washed with 50 cm3 of a 10% aqueous solution of sodium thiosulphate and then with 50 cm3 of a saturated aqueous solution of sodium hydrogen carbonate. The organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The crystalline residue is washed with ethyl ether, drained and dried under reduced pressure (2.7 kPa). 1.3 g of 3,4-dihydro-4,4-diphenyl2H-thiapyran 1,1-dioxide are obtained in the form of white crystals; melting point 166° C.

Workup

  1. washis washed with 50 cm3 of a 10% aqueous solution of sodium thiosulphate
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. washThe crystalline residue is washed with ethyl ether
  5. customdried under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-8e2d9cf8160e43d68052a78be378b589
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

Loading…