Methyl iodide → HCID 10021837, compound

HRID 1029547Notes

Reaction equation

HRID 1029547 reaction equation
[OH-].[Na+].[CH3:3][C:4]([C:7]1[CH:8]=[C:9]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[O:10][CH2:11][C:12]1[S:16][C:15](=[S:17])[NH:14][N:13]=1)([CH3:6])[CH3:5].I[CH3:27]>CO>[CH3:23][C:22]([C:19]1[CH:18]=[C:9]([O:10][CH2:11][C:12]2[S:16][C:15]([S:17][CH3:27])=[N:14][N:13]=2)[CH:8]=[C:7]([C:4]([CH3:3])([CH3:5])[CH3:6])[C:20]=1[OH:21])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 10316027HCID 10316027, compound

Product 1

HCID 10021837HCID 10021837, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1N sodium hydroxide (1.05 mL, 1.05 mmol) is added over 5 minutes to a solution of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenoxy]-methyl]-1,3,4-thiadiazole-2(3H)-thione (0.37 g, 1.05 mmol) and iodomethane (0.26 mL, 4.20 mmol) in methanol (10 mL). The reaction is stirred for 30 minutes, then the pink precipitate is filtered and washed with methanol/water. A second crop is collected, and the combined precipitate is (71%) of pink platelets which are 2,6-bis(1,1-dimethylethyl)-4-[(5-methylthio-1,3,4-thiadiazol-2-yl)methoxy]phenol; mp 128.0°-129.5° C.

Workup

  1. filtrationthe pink precipitate is filtered
  2. washwashed with methanol/water
  3. customA second crop is collected

Sources & evidence

ORD record
ord-acfbf61b15e84a80b90bc667136e2f75
Source dataset
uspto-grants-1992_04
Patent number
US05102897

Reaction notes

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