Sodium hydride → 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine

15 g of dimercaptobenzene were slowly added dropwise while cooling to 5.55 g of sodium hydride (50% in mineral oil) in 150 ml of dimethyl sulfoxide, whereby the internal temperature was held between 15° and 23° C. Subsequently, the reaction mixture was stirred at room temperature for 1 hour and cooled with ice/methanol. Thereafter, 50 g of 2,2-dimethylpropanediol ditosylate in solid form were added in one portion and the reaction mixture was heated to 80° C. for 3 hours. Thereafter, the reaction mixture was cooled, poured on to ice, extracted with ether, the extract was washed with water and dried. After evaporation of the solvent, there was obtained a yellow oil which was chromatographed on silica gel (petroleum ether/ethyl acetate 99:1). There were obtained 14 g of 3,4-dihydro-3,3-dimethyl-2H-1,5-benzodithiepine as a colorless oil.

1. customwas held between 15° and 23° C
2. temperaturethe reaction mixture was heated to 80° C. for 3 hours
3. temperatureThereafter, the reaction mixture was cooled
4. additionpoured on to ice
5. extractionextracted with ether
6. washthe extract was washed with water
7. customdried
8. customAfter evaporation of the solvent
9. customthere was obtained a yellow oil which
10. customwas chromatographed on silica gel (petroleum ether/ethyl acetate 99:1)

ORD record

ord-bee86677d3cf4bfaad6c842329a5d0a4

Source dataset

uspto-grants-1992_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05164387