Methyl iodide → HCID 178503407, compound

HRID 1982133Notes

Reaction equation

HRID 1982133 reaction equation
[H-].[Na+].[SH:3][C:4]1[NH:8][N:7]=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[N:5]=1.[CH3:19]I>O1CCCC1>[CH3:19][S:3][C:4]1[NH:8][N:7]=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178526583HCID 178526583, compound

Product 1

HCID 178503407HCID 178503407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.61 g of sodium hydride in 50 ml of tetrahydrofuran, 5 g of 5-mercapto-3-(o-nitrobenzyl)-1,2,4-triazole is added in portions with stirring at room temperature over a period of 30 minutes. The mixture is stirred for 2 hours, 1.51 ml of methyl iodide is added at once, the mixture is stirred overnight at room temperature and evaporated to dryness in vacuo. The residue is treated with water and methylene chloride, the aqueous layer is extracted once more with methylene chloride, the combined organic extracts are dried over magnesium sulfate, evaporated to a small volume and diluted with ether to give 5-methylmercapto-3-(o-nitrobenzyl)-1,2,4-triazole, m.p. 120°-132°.

Workup

  1. additionis added in portions
  2. stirringThe mixture is stirred for 2 hours
  3. stirringis stirred overnight at room temperature
  4. customevaporated to dryness in vacuo
  5. additionThe residue is treated with water and methylene chloride
  6. extractionthe aqueous layer is extracted once more with methylene chloride
  7. dry with materialthe combined organic extracts are dried over magnesium sulfate
  8. customevaporated to a small volume
  9. additiondiluted with ether

Sources & evidence

ORD record
ord-7d175ef8bd3a41b0b435e04428a54f9b
Source dataset
uspto-grants-1986_06
Patent number
US04595535

Reaction notes

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