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-3aa570b095d741d3b2f2b2e26bd801b6

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05420273