Triethylamine → HCID 20232062, compound

HRID 2290352Notes

Reaction equation

HRID 2290352 reaction equation
ClC(OCC)=O.[CH2:7]([O:9][C:10]([NH:12][CH2:13][C:14]([OH:16])=O)=[O:11])[CH3:8].C(N(CC)CC)C.[NH:24]([C:26]1[N:27]=[N:28][C:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:30]([CH3:32])[N:31]=1)[NH2:25]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:7]([O:9][C:10]([NH:12][CH2:13][C:14]([NH:25][NH:24][C:26]1[N:27]=[N:28][C:29]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[C:30]([CH3:32])[N:31]=1)=[O:16])=[O:11])[CH3:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 96472Glycine, N-(ethoxycarbonyl)-HCID 15586409HCID 15586409, compound

Product 1

HCID 20232062HCID 20232062, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl chloroformate (3.689 g) in methylene chloride (10 ml) was added dropwise to a stirred solution of N-ethoxycarbonylglycine (4.998 g) and triethylamine (3.434 g) in methylene chloride (60 ml) under cooling in 5 minutes, and the stirring was continued for 5 minutes under cooling. To the solution of the mixed anhydride was added a solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (3.417 g) in chloroform (40 ml) and reacted in a similar manner to that of Example 17-(1). The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated under reduced pressure. The residue was dissolved in ethanol (50 ml) and a solution of sodium hydroxide (1.6 g) in water (10 ml) was added dropwise to the solution with stirring under ice cooling in 5 minutes. After stirring for 30 minutes at room temperature, the solution was evaporated, and the residue was dissolved in a small amount of water. The solution was salted out and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and evaporated. The residue was dissolved in chloroform containing a small amount of ethanol and the solution was chromatographed on silica gel (50 g). The eluent with a mixture of chloroform and ethanol (30:1) gave a colorless solid of 3-[2-(N-ethoxycarbonylglycyl)hydrazino]-5-methyl-6-phenyl-1,2,4-triazine (1.872 g).

Workup

  1. temperatureunder cooling in 5 minutes
  2. temperatureunder cooling
  3. customreacted in a similar manner to that of Example 17-(1)
  4. washThe reaction mixture was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (50 ml)
  8. additiona solution of sodium hydroxide (1.6 g) in water (10 ml) was added dropwise to the solution
  9. stirringAfter stirring for 30 minutes at room temperature
  10. customthe solution was evaporated
  11. dissolutionthe residue was dissolved in a small amount of water
  12. extractionextracted with ethyl acetate
  13. washThe extract was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over magnesium sulfate
  15. customevaporated
  16. dissolutionThe residue was dissolved in chloroform containing a small amount of ethanol
  17. customthe solution was chromatographed on silica gel (50 g)
  18. additionThe eluent with a mixture of chloroform and ethanol (30:1)

Sources & evidence

ORD record
ord-492ba0e63be44ff9ac0c2d97ef843826
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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