Ethyl Bromide → HCID 13867659, compound

To a solution of 2.88 g of 6,7-dichloro-2-hydroxymethyl-2,3-dihydrobenzofuran dissolved in 22 ml of DMF is added 790 mg of sodium hydride (50% suspension) and stirred at room temperature for 30 minutes. After addition of 1.73 g of ethyl bromide, the reaction mixture is stirred at room temperature for 17 hours and extracted with water and ether. The ether layer is washed with water, dried over magensium sulfate, and evaporated under reduced pressure to give a residue, which is chromatographed on silica gel with dichloromethane as an eluent to give 2.0 g of oily 6,7-dichloro-2-ethoxymethyl-2,3-dihydrobenzofuran. To a solution of 2.0 g of the 6,7-dichloro-2-ethoxymethyl-2,3-dihydrobenzofuran dissolved in 5 ml of thionyl chloride is dropwise added 3 g of chlorosulfonic acid under ice-cooling. The reaction mixture is stirred at room temperature for 2 hours, then poured into iced water, and extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried and evaporated under reduced pressure to give an oil, which is then dissolved in 30 ml of dichloromethane. After introduction of 30 ml of ammonia at -30° to -20° C., the mixture is allowed to stand at room temperature for a night and evaporated under reduced pressure to give an oily residue, which is then dissolved in ethyl acetate and washed with water. The ethyl acetate layer is dried and evaporated to dryness to give 2.7 g of an oily product, which is chromatographed on silica gel with dichloromethane (1000 ml) and successively dichloromethane/acetone (20/1) as eluents to give 900 mg of the objective 6,7-dichloro-2-ethoxymethyl-5-sulfamoyl-2,3-dihydrobenzofuran (I j-84) as crystals, yield 24%, m.p. 148°-149° C.

1. stirringthe reaction mixture is stirred at room temperature for 17 hours
2. extractionextracted with water and ether
3. washThe ether layer is washed with water
4. dry with materialdried over magensium sulfate
5. customevaporated under reduced pressure
6. customto give a residue, which
7. customis chromatographed on silica gel with dichloromethane as an eluent

ORD record

ord-00f3170d25364330976d0ba6eb6a887f

Source dataset

uspto-grants-1987_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04659709