Methanol → 3-Methoxy-5,6-bis(4-methoxyphenyl)-1,2,4-triazine

HRID 1449411Notes

Reaction equation

HRID 1449411 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12](SC)[N:13]=[N:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[CH:6][CH:5]=1.[CH3:26][OH:27]>C(OCC)C>[CH3:26][O:27][C:12]1[N:13]=[N:14][C:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[N:11]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 6172401,2,4-Triazine, 5,6-bis(4-methoxyphenyl)-3-(methylthio)-HCID 5360545Sodium

Product 1

HCID 126766093-Methoxy-5,6-bis(4-methoxyphenyl)-1,2,4-triazine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Sodium, 3.0 g. (0.13 mole), was added piecewise under a nitrogen atmosphere to 100 ml. of dry methanol, followed by the addition of a slurry of 31.6 g. (0.1 mole) of 5,6-bis(4-methoxyphenyl)-3-methylthio-1,2,4-triazine in methanol. The reaction mixture was heated at reflux overnight. The reaction mixture was cooled and filtered. The filter cake and filtrate were extracted with diethyl ether. The diethyl ether was concentrated, giving a solid, m.p. >220° C. The solid was taken up in diethyl ether and the insoluble material was removed by filtration. The filtrate was dried over anhydrous sodium sulfate and concentrated to give a solid residue which was recrystallized from petroleum ether to give 3-methoxy-5,6-bis(4-methoxyphenyl)-1,2,4-triazine, m.p. about 105°-108° C.

Workup

  1. addition(0.13 mole), was added piecewise under a nitrogen atmosphere to 100 ml
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux overnight
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. extractionThe filter cake and filtrate were extracted with diethyl ether
  7. concentrationThe diethyl ether was concentrated
  8. customgiving a solid, m.p. >220° C
  9. customthe insoluble material was removed by filtration
  10. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customto give a solid residue which
  13. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-7ed773e648a9458cb033aea4d90136f6
Source dataset
uspto-grants-1980_02
Patent number
US04190725

Reaction notes

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