Dimethylformamide → 2-Phenyl-4-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile

HRID 880044Notes

Reaction equation

HRID 880044 reaction equation
[C:1]1([N:7]2[C:12](=[O:13])[NH:11][C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17]N(C=O)C.[H-].[Na+].CI>O>[C:1]1([N:7]2[C:12](=[O:13])[N:11]([CH3:17])[C:10](=[O:14])[C:9]([C:15]#[N:16])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 563387HCID 563387, compound

Product 1

HCID 47801582-Phenyl-4-methyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Intermediate c (9 g, 0.042 mol) was added to DMF (100 mL). To the mixture was added NaH (1.3 g, 0.054 mol) in batch under an ice bath. After stirring for 30 min, methyl iodide (2.74 mL, 0.042 mol) was added dropwise. After the dropwise addition, the reaction was conducted for 2 h. After completion of the reaction, the reaction solution was poured into water (600 mL). A great deal of red solid separated out and was filtered by suction. The filtered cake was washed with water and dried to produce an orange red solid (7.6 g) in a yield of 80.0%.

Workup

  1. additionAfter the dropwise addition
  2. waitthe reaction was conducted for 2 h
  3. customAfter completion of the reaction
  4. customA great deal of red solid separated out
  5. filtrationwas filtered by suction
  6. washThe filtered cake was washed with water
  7. customdried

Sources & evidence

ORD record
ord-75f89cc42dbd4531b2adc0ab4912e8f1
Source dataset
uspto-grants-2015_03
Patent number
US08993566B2

Reaction notes

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