Ethanolamine → 3-(2-Hydroxyethylamino)-5-methyl-6-phenyl-1,2,4-triazine

HRID 2290332Notes

Reaction equation

HRID 2290332 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]([CH2:18][NH2:19])[OH:17]>C(OCC)(=O)C>[OH:17][CH2:16][CH2:18][NH:19][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

Participants

4

Reactant 2

HCID 700EthanolamineHCID 15586342HCID 15586342, compound

Product 1

HCID 202320443-(2-Hydroxyethylamino)-5-methyl-6-phenyl-1,2,4-triazineYield 88.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-methyl-3-methylthio-6-phenyl-1,2,4-triazine (3 g) and ethanolamine (3 g) was heated at 150° to 160° C. for 5.25 hours. The reaction mixture was dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was crystallized from a small amount of diethyl ether and then diisopropyl ether was added thereto. The crystals were collected by filtration, washed with diisopropyl ether and dried to give 3-(2-hydroxyethylamino)-5-methyl-6-phenyl-1,2,4-triazine (2.82 g).

Workup

  1. temperaturewas heated at 150° to 160° C. for 5.25 hours
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from a small amount of diethyl ether
  6. additiondiisopropyl ether was added
  7. filtrationThe crystals were collected by filtration
  8. washwashed with diisopropyl ether
  9. customdried

Sources & evidence

ORD record
ord-b64fa805616a4e49bfe0c5a256ad50b2
Source dataset
uspto-grants-1986_10
Patent number
US04616014

Reaction notes

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