Triethylamine → HCID 20232065, compound

HRID 2290351Notes

Reaction equation

HRID 2290351 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH:8]([C:10]1[N:11]=[N:12][C:13]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:14]([CH3:16])[N:15]=1)[NH2:9].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][C:14]1[N:15]=[C:10]([NH:8][NH:9][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][CH3:1])[N:11]=[N:12][C:13]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 15586409HCID 15586409, compound

Product 1

HCID 20232065HCID 20232065, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of n-valeryl chloride (1.93 g) in methylene chloride (3 ml) was added dropwise to a stirred solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (3.224 g) and triethylamine (1.784 g) in methylene chloride (40 ml) under ice cooling, and the stirring was continued for 30 minutes. The reaction mixture was evaporated and the resultant residue was extracted with ethyl acetate after addition of water. The extract was washed successively with 5% hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and water, dried over magnesium sulfate, and then concentrated to a small volume under reduced pressure. The resultant residue was crystallized from diethyl ether, collected by filtration, washed with diethyl ether and dried to give 5-methyl-6-phenyl-3-(2-valerylhydrazino)-1,2,4-triazine (3.406 g).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionthe resultant residue was extracted with ethyl acetate
  3. additionafter addition of water
  4. washThe extract was washed successively with 5% hydrochloric acid, water
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and water, dried over magnesium sulfate
  6. concentrationconcentrated to a small volume under reduced pressure
  7. customThe resultant residue was crystallized from diethyl ether
  8. filtrationcollected by filtration
  9. washwashed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-550a18e95d614adca2c00386aa8c2c24
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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