Water → 2,6-Di-tert-butyl-4-[2-(methylsulfanyl)-1,3-thiazol-4-yl]phenol

HRID 980342Notes

Reaction equation

HRID 980342 reaction equation
[Na].[C:2]([C:6]1[CH:7]=[C:8]([C:17]2[N:18]=[C:19]([SH:22])[S:20][CH:21]=2)[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:5])([CH3:4])[CH3:3].[CH3:23]I.O>CO>[C:2]([C:6]1[CH:7]=[C:8]([C:17]2[N:18]=[C:19]([S:22][CH3:23])[S:20][CH:21]=2)[CH:9]=[C:10]([C:13]([CH3:15])([CH3:16])[CH3:14])[C:11]=1[OH:12])([CH3:3])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 5360545SodiumHCID 178440667HCID 178440667, compound

Product 1

HCID 135636842,6-Di-tert-butyl-4-[2-(methylsulfanyl)-1,3-thiazol-4-yl]phenolYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 30 ml of methanol was dissolved 0.18 g of metallic sodium and after adding thereto 2.1 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-mercaptothiazole, 1.15 g of methyl iodide was added dropwise to the solution at 0°-5° C. After allowing to stand the mixture for 30 minutes at room temperature, 60 ml of iced water was added to the reaction mixture. The crystals thus precipitated were recovered by filtration and recrystallized from n-hexane to provide 1.6 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-methylthiothiazole.

Workup

  1. additionafter adding
  2. customfor 30 minutes
  3. customat room temperature
  4. customThe crystals thus precipitated
  5. filtrationwere recovered by filtration
  6. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-0762dd56bf254c5297726d5332ddfa90
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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