Toluene → HCID 13774876, compound

Temperature

0 °C

47% ethyl glyoxylate in toluene (polymer type) (467.84 g, 2.15 mol) was dissolved in THF (620 ml), to the solution was slowly added methylhydrazine (103 g, 1.02 eq) under ice-cooled. After the addition was complete, the mixture was stirred at 0° C. for 30 minutes and at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in toluene (400 ml), and concentrated under reduced pressure. The resulting solid was washed with tert-butyl methyl ether (200 ml), and allowed to stand at 0° C. for 30 minutes. Then, the mixture was filtered, and washed with cooled tert-butyl methyl ether (100 ml) to give 223.91 g of Compound (XVI-1) (yield: 78.8%) as solid.

1. temperaturecooled
2. additionAfter the addition
3. concentrationThe reaction solution was concentrated under reduced pressure
4. dissolutionThe residue was dissolved in toluene (400 ml)
5. concentrationconcentrated under reduced pressure
6. washThe resulting solid was washed with tert-butyl methyl ether (200 ml)
7. waitto stand at 0° C. for 30 minutes
8. filtrationThen, the mixture was filtered
9. washwashed with cooled tert-butyl methyl ether (100 ml)

ORD record

ord-36e32fb4bd774673a9326c9fe2c80b2a

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029295B2