Methyl iodide → HCID 135712889, compound

HRID 1296716Notes

Reaction equation

HRID 1296716 reaction equation
[C:1]1([C:7]2[CH:16]=[C:10]3[NH:11][C:12](=[S:15])[NH:13][CH2:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:17].[Na+].I[CH3:20]>C(O)C>[CH3:20][S:15][C:12]1[NH:13][C:14](=[O:17])[N:9]2[N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:16]=[C:10]2[N:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 136375618HCID 136375618, compound

Product 1

HCID 135712889HCID 135712889, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7-Phenyl-2-thioxo-2,3-dihydropyrazolo[1,5-a][1,3,5]triazin-4(1H-one (6.4 g, 26.2 mmol) was dissolved in absolute ethanol (150 mL). To this solution was added aqueous sodium hydroxide (2.1 g, 53 mmol in 50 mL of water) and finally iodomethane (1.7 mL, 27.3 mmol) was added dropwise. The resulting solution was stirred at room temperature for 3 hours and then concentrated to a white solid. This solid was suspended in water and the mixture acidified (to pH=1) with concentrated sulfuric acid. The resulting precipitate was collected by filtration, washed with water and dried to give 2-(methylsulfanyl)-7-phenylpyrazolo[1,5-a][1,3,5]triazin-4(3H)-one (5.5 g, 81%) as a white solid. 1H-NMR (DMSO-d6): δ 7.99 (d, 2H), 7.5 (m, 3H), 6.93 (s, 1H), 2.58 (s, 3H); MS m/z 259 (M+1).

Workup

  1. additionwas added dropwise
  2. concentrationconcentrated to a white solid
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ed1d04dc64ae484aabbc95ae30bfb46b
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Reaction notes

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