N,N-Diethylethylenediamine → HCID 15586343, compound

HRID 2290328Notes

Reaction equation

HRID 2290328 reaction equation
[CH3:1][C:2]1[N:3]=[C:4](SC)[N:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][NH2:21])[CH3:17]>C(OCC)(=O)C>[CH2:16]([N:18]([CH2:22][CH3:23])[CH2:19][CH2:20][NH:21][C:4]1[N:5]=[N:6][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:2]([CH3:1])[N:3]=1)[CH3:17]

Participants

4

Reactant 2

HCID 60993N,N-DiethylethylenediamineHCID 15586342HCID 15586342, compound

Product 1

HCID 15586343HCID 15586343, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-methyl-3-methylthio-6-phenyl-1,2,4-triazine (2.17 g) and N,N-diethylethylenediamine (2.99 g) was heated at 150° C. to 160° C. for 17 hours. The reaction mixture was dissolved in ethyl acetate, washed with water and brine, and then dried over sodium sulfate, which was treated with silical gel and filtered by suction. The filtrate was evaporated to dryness and the resulting residue was crystallized with diisopropyl ether under ice cooling. The resultant crystals were collected by filtration, washed with diisopropyl ether and dried to give 3-(2-diethylaminoethylamino)-5-methyl-6-phenyl-1,2,4-triazine (1.83 g).

Workup

  1. temperaturewas heated at 150° C. to 160° C. for 17 hours
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate, which
  4. additionwas treated with silical gel
  5. filtrationfiltered by suction
  6. customThe filtrate was evaporated to dryness
  7. customthe resulting residue was crystallized with diisopropyl ether under ice cooling
  8. filtrationThe resultant crystals were collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried

Sources & evidence

ORD record
ord-84a4d49dab77482ba1236ee2ec78797d
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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