Methyl iodide → HCID 135786541, compound

HRID 466067Notes

Reaction equation

HRID 466067 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[N:20]=[N:19][C:18](=[S:21])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].I[CH3:23].[OH-].[Na+]>C(O)C>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([C:16]2[NH:20][N:19]=[C:18]([S:21][CH3:23])[N:17]=2)[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 1357865375-[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]-3H-1,2,4-triazole-3-thione

Product 1

HCID 135786541HCID 135786541, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6.00 g (19.64 mmol) of triazolethione (Example 19) and 9.1 g (60.0 mmol) of iodomethane in 50 ml of absolute ethanol is stirred at 50° to 60° C. for 0.5 hour, then cooled to room temperature. The reaction is treated with 300 ml aqueous 0.7N NaOH, stirred for 30 minutes, and filtered. Recrystallization of the resulting solid from ethanol-water gives 5.26 g (6.27 g theor., 84%) of the S-methylated product as a fluffy, white solid, mp 271°-272° C.

Workup

  1. filtrationfiltered
  2. customRecrystallization of the resulting solid from ethanol-water
  3. customgives 5.26 g (6.27 g theor., 84%) of the S-methylated product as a fluffy, white solid, mp 271°-272° C.

Sources & evidence

ORD record
ord-67c5aabbc862473e8ad834607a43c1cf
Source dataset
uspto-grants-1992_10
Patent number
US05155122

Reaction notes

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