Dimethylformamide → HCID 21484901, compound

HRID 1414714Notes

Reaction equation

HRID 1414714 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][C:4](=[S:8])[N:3]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CN(C)C=O.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C([O-])([O-])=O.[K+].[K+].O>[CH2:9]([N:3]1[C:4]([S:8][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:5][CH2:6][CH2:7][N:2]1[CH3:1])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 214848962-Benzyl-1-methyl-1,2,4-triazinane-3-thione

Product 1

HCID 21484901HCID 21484901, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 11430Potassium CarbonateSolvent2×

Conditions

Temperature
35 °C

Procedure

Seven grams of tetrahydro-1-methyl-2-(phenylmethyl)-1,2,4-triazine-3(2H)-thione was dissolved in 30 ml. of dimethyl formamide. Three grams of finely ground potassium carbonate (K2CO3) was added to the solution. Benzyl bromide (5.43 grams) was added in several additions at room temperature. The mixture was heated to 60°-65° C and held at that temperature for 2 hours. The mixture was chilled and diluted with additional K2CO3 (10 g.) and water (200 ml). The product was extracted with trichloromethane and washed with brine. The mixture was dried with magnesium sulfate. The mixture was diluted with ethyl ether and the insoluble particles filtered off. The filtrate was heated to 35° C to concentrate the solution. Upon chilling 2-benzyl-3-(benzylthio)-1,2,5,6-tetrahydro-1-methyl-1,2,4-triazine crystallized from the liquid reaction mass. This product was recrystallized from isopropanol-hexane. The product was found to have a melting point at 45° C. The structure was confirmed by IR, NMR and elemental analysis.

Workup

  1. temperatureThe mixture was heated to 60°-65° C
  2. temperatureThe mixture was chilled
  3. extractionThe product was extracted with trichloromethane
  4. washwashed with brine
  5. dry with materialThe mixture was dried with magnesium sulfate
  6. additionThe mixture was diluted with ethyl ether
  7. filtrationthe insoluble particles filtered off
  8. concentrationto concentrate the solution
  9. temperatureUpon chilling 2-benzyl-3-(benzylthio)-1,2,5,6-tetrahydro-1-methyl-1,2,4-triazine
  10. customcrystallized from the liquid reaction mass
  11. customThis product was recrystallized from isopropanol-hexane
  12. customat 45° C

Sources & evidence

ORD record
ord-3dd537573a3540adba0a7c5c3f2d43d6
Source dataset
uspto-grants-1977_01
Patent number
US04002624

Reaction notes

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