Triethylamine → HCID 53899066, compound

A solution of ethyl chloroformate (1.628 g) in methylene chloride (6 ml) was added dropwise to a stirred solution of acetoxyacetic acid (1.77 g) and triethylamine (1.515 g) in methylene chloride (30 ml) under ice cooling in 3 minutes, and the stirring was continued for 10 minutes under ice cooling. To the mixture was added quickly a solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (2.01 g) in chloroform (28 ml) with stirring under ice cooling, and then the stirring was continued for 20 minutes. The solution was washed with water, dried over sodium sulfate, and concentrated. The resultant residue was dissolved in methanol (50 ml), and a solution of sodium hydroxide (0.8 g) in water (10 ml) was added thereto under ice cooling. After stirring for 0.5 hours, the solution was evaporated under reduced pressure and the residue was dissolved in water. To the solution was added dry ice and then the solution was concentrated under reduced pressure. The resultant precipitates were collected by filtration, washed with cold water and dried. On the other hand, the filtrate was salted out and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated to give a solid residue. The residue was combined with the substance obtained above, and recrystallized from a mixture of ethyl acetate and ethanol to give colorless crystals of 3-(2-hydroxyacetylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine (1.852 g).

1. waitthe stirring was continued for 20 minutes
2. washThe solution was washed with water
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated
5. dissolutionThe resultant residue was dissolved in methanol (50 ml)
6. additiona solution of sodium hydroxide (0.8 g) in water (10 ml) was added
7. stirringAfter stirring for 0.5 hours
8. customthe solution was evaporated under reduced pressure
9. dissolutionthe residue was dissolved in water
10. additionTo the solution was added dry ice
11. concentrationthe solution was concentrated under reduced pressure
12. customThe resultant precipitates
13. filtrationwere collected by filtration
14. washwashed with cold water
15. customdried
16. extractionextracted with ethyl acetate
17. dry with materialThe extract was dried over magnesium sulfate
18. customevaporated
19. customto give a solid residue
20. customobtained above, and
21. customrecrystallized from a mixture of ethyl acetate and ethanol

ORD record

ord-c4c417f294e34c0784a4cea73652e20e

Source dataset

uspto-grants-1986_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04616014