Triethylamine → 3-(2-Ethoxycarbonylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine

HRID 2290344Notes

Reaction equation

HRID 2290344 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH:7]([C:9]1[N:10]=[N:11][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:13]([CH3:15])[N:14]=1)[NH2:8].C(N(CC)CC)C>C(Cl)Cl>[CH2:5]([O:4][C:2]([NH:8][NH:7][C:9]1[N:10]=[N:11][C:12]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:13]([CH3:15])[N:14]=1)=[O:3])[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 15586409HCID 15586409, compound

Product 1

HCID 202320283-(2-Ethoxycarbonylhydrazino)-5-methyl-6-phenyl-1,2,4-triazineYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of ethyl chloroformate (1.98 g) in methylene chloride (5 ml) was added dropwise to a stirred solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (3.68 g) in methylene chloride (40 ml) under ice cooling in 15 minutes, and the reaction mixture was treated with a solution of triethylamine (1.8 g) in methylene chloride (10 ml) under ice cooling. The reaction mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate after addition of water. The extract was washed with 5% hydrochloric acid and water, dried over magnesium sulfate, concentrated under reduced pressure, and the residue was pulverized with diisopropyl ether. The resulting precipitates were collected by filtration, washed with water and dried to give 3-(2-ethoxycarbonylhydrazino)-5-methyl-6-phenyl-1,2,4-triazine (3.23 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. additionafter addition of water
  4. washThe extract was washed with 5% hydrochloric acid and water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-a4d1490ab0ba4303adbccb320a84826e
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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