Triethylamine → N-(2-Chloroethyl)-2-furamide

To a stirred and cooled (ice-bath) mixture of 87 parts of 2-chloroethanamine hydrochloride and 300 parts of trichloromethane are added 224.2 parts of N,N-diethylethanamine, there is added dropwise, during a 1.50 hours period, a solution of 96 parts of 2-furancarbonyl chloride in 300 parts of trichloromethane at a temperature below 5° C. Upon completion, stirring is continued overnight at room temperature. The reaction mixture is poured onto water and the layers are separated. The aqueous phase is extracted with trichloromethane. The combined organic phases are washed with water, with a diluted hydrochloric acid solution and again twice with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 2% of methanol as eluent. The pure fractions are collected and the eluent is evaporated, yielding 95 parts of N-(2-chloroethyl)-2-furancarboxamide as a residue.

1. temperaturecooled
2. additionis added dropwise, during a 1.50 hours period
3. customat a temperature below 5° C
4. stirringUpon completion, stirring
5. additionThe reaction mixture is poured onto water
6. customthe layers are separated
7. extractionThe aqueous phase is extracted with trichloromethane
8. washThe combined organic phases are washed with water, with a diluted hydrochloric acid solution and again twice with water
9. customdried
10. filtrationfiltered
11. customevaporated
12. customThe residue is purified by column-chromatography over silica gel using
13. additiona mixture of trichloromethane and 2% of methanol as eluent
14. customThe pure fractions are collected
15. customthe eluent is evaporated

ORD record

ord-69ade960960342918b64a91a89f0bd6d

Source dataset

uspto-grants-1977_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04031226