Benzene → HCID 15230361, compound

Temperature

90 °C

A solution of 30 g of 2,4-dibromobutyryl chloride (J. Med. Chem., p1995, 30. 1987) and 13.63 g of urea dissolved into 150 ml of benzene was heated at 90° C. with stirring for 3 hours. The reaction mixture was cooled to room temperature, then a very excessive amount of ethyl acetate was added thereto. The layer of ethyl acetate was washed with an aqueous solution of sodium bicarbonate and saturated brine, then the resulting solution was dried over magnesium sulfate and evaporated. The obtained residue (28 g) was dissolved into 30 ml of tetrahydrofuran (THF) and cooled. To this mixture was added 4.7 g of NaH (55% in mineral oil) bit by bit, then the mixture was stirred at room temperature for 2 hours. The reaction mixture was evaporated to make the amount of the solution about 50 ml, then which was poured into ethyl acetate. The layer of ethyl acetate was washed with water and saturated brine, dried over magnesium sulfate, and evaporated. The obtained residue was washed well with n-hexane, whereby 15.7 g of the objective compound was obtained in 66% yield.

1. temperatureThe reaction mixture was cooled to room temperature
2. washThe layer of ethyl acetate was washed with an aqueous solution of sodium bicarbonate and saturated brine
3. dry with materialthe resulting solution was dried over magnesium sulfate
4. customevaporated
5. dissolutionThe obtained residue (28 g) was dissolved into 30 ml of tetrahydrofuran (THF)
6. temperaturecooled
7. additionTo this mixture was added 4.7 g of NaH (55% in mineral oil) bit by bit
8. stirringthe mixture was stirred at room temperature for 2 hours
9. customThe reaction mixture was evaporated
10. additionwhich was poured into ethyl acetate
11. washThe layer of ethyl acetate was washed with water and saturated brine
12. dry with materialdried over magnesium sulfate
13. customevaporated
14. washThe obtained residue was washed well with n-hexane

ORD record

ord-c4dd482fd68f47068d615676e98c3fb8

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05319099