Dimethylformamide → HCID 19994815, compound

To a stirred solution of 25 parts of 3-methyl-2,4-imidazolidinedione in 198 parts of N,N-dimethylformamide were added portionwise 1.6 parts of a sodium hydride dispersion 50% under nitrogen atmosphere (exothermic reaction, cooling). Upon complete addition, stirring was continued for 1 hour at room temperature. 45.5 Parts of 1,2-dibromoethane were added dropwise. Upon completion, the whole was stirred for 2 days at room temperature. The reaction mixture was evaporated and the residue was taken up in a mixture of water and dichloromethane. The separated organic layer was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 35.8 parts (73.6%) of 3-(2-bromoethyl)-1-methyl-2,4-imidazolidinedione as a residue (int. 33).

1. custom(exothermic reaction, cooling)
2. additionUpon complete addition
3. stirringUpon completion, the whole was stirred for 2 days at room temperature
4. customThe reaction mixture was evaporated
5. additionthe residue was taken up in a mixture of water and dichloromethane
6. customThe separated organic layer was dried
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by column chromatography over silica gel using
10. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
11. customThe pure fractions were collected
12. customthe eluent was evaporated

ORD record

ord-f5c84e403e2142f09d77d1a80ca28a14

Source dataset

uspto-grants-1990_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04975439