Chloroform → HCID 19907444, compound

To 40 ml of chloroform were added 4.0 g of methyl 4-mercaptobenzoate, 3.3 g of 3-bromo-1-propanol and 2.38 g of triethylamine, and the mixture was stirred for an hour and then evaporated under a reduced pressure. After adding 50 ml of ethyl acetate, the mixture was washed with 30 ml each of water, 1N hydrochloric acid and a saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate and evaporated under a reduced pressure. The residue was applied to a silica gel column and eluted with chloroform/methanol (100:3) to obtain 3.6 g of methyl p-(3-hydroxypropylthio)benzoate as a colorless crystal. To 3.0 g of this crystal was added 1.44 g of phosphorus tribromide, and the mixture was heated at 80° C. for 2 hours, poured into 50 ml of ice-water, and extracted three times with 20 ml of ethyl acetate. The extract was dried over magnesium sulfate, and evaporated under a reduced pressure. The residue was applied to a silica gel column and eluted with chloroform/hexane (1:1) to obtain 3.0 g of the title compound as a colorless oil.

1. customevaporated under a reduced pressure
2. additionAfter adding 50 ml of ethyl acetate
3. washthe mixture was washed with 30 ml each of water, 1N hydrochloric acid
4. dry with materiala saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate
5. customevaporated under a reduced pressure
6. washeluted with chloroform/methanol (100:3)

ORD record

ord-ef40bdac534b47579875a355d77ec551

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05093370