Diazomethane → HCID 53710760, compound

Diethylether (300 ml) was added to trifluoroacetoacetonitrile (13.7 g, 0.100 mole) and to this was added an ethereal solution of diazomethane, which was prepared from N-nitrosomethylurea (25.77 g, 0.250 mole), a 50% solution of potassium hydroxide (112.22 g, 1.00 mole) and diethylether (180 ml), with ice cooling. The solution was allowed to stand over night while cooling with ice. Next day, until the pH being 3-4 (by an universal test paper) acetic acid in limited amounts was added to the reaction mixture to decompose an excess of diazomethane and the solution was concentrated to about 200 ml at atmospheric pressure by using a distillation apparatus equipped with a fractionating column. The concentrate was washed with a 8% solution of sodium bicarbonate and water and dried with anhydrous sodium sulfate. Diethyl ether was distilled off by using a distillation apparatus equipped with a fractionating column at atmospheric pressure and the residue was distilled under reduced pressure to give the title compound (5.31 g, 35.1%) as a colorless liquid, b.p. 58.0° C./68 mmHg-64.0° C./70.0 mmHg. The structure of the product was confirmed by IR and NMR.

1. waitto stand over night
2. temperaturewhile cooling with ice
3. additionwas added to the reaction mixture
4. concentrationthe solution was concentrated to about 200 ml at atmospheric pressure
5. customequipped with a fractionating column
6. washThe concentrate was washed with a 8% solution of sodium bicarbonate and water
7. dry with materialdried with anhydrous sodium sulfate
8. distillationDiethyl ether was distilled off
9. customequipped with a fractionating column at atmospheric pressure
10. distillationthe residue was distilled under reduced pressure

ORD record

ord-45159e07cb4b47a286d72e4f2f8ab225

Source dataset

uspto-grants-1989_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04797492