Potassium Carbonate → 2,6-Di-tert-butyl-4-(5-methyl-1,3-thiazol-4-yl)phenol

HRID 980332Notes

Reaction equation

HRID 980332 reaction equation
[CH:1]([NH2:3])=[S:2].Br[CH:5]([CH3:23])[C:6]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:19]([C:10]1[CH:9]=[C:8]([C:6]2[N:3]=[CH:1][S:2][C:5]=2[CH3:23])[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]=1[OH:18])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 3005587MethanethioamideHCID 13173168HCID 13173168, compound

Product 1

HCID 131070202,6-Di-tert-butyl-4-(5-methyl-1,3-thiazol-4-yl)phenolYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.7 g of thioformamide, 3.4 g of 4-(2-bromopropionyl)-2,6-di-tert-butylphenol, and 15 ml of absolute ethanol was heated to 50°-60° C. for 2-3 hours. After cooling, the reaction mixture poured into a diluted aqueous solution of potassium carbonate. The precipitates thus formed were recovered by filtration and recrystallized from a mixture of cyclohexane and hexane to provide 1.2 g of 4-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methylthiazole.

Workup

  1. temperaturewas heated to 50°-60° C. for 2-3 hours
  2. temperatureAfter cooling
  3. customThe precipitates thus
  4. customformed
  5. filtrationwere recovered by filtration
  6. customrecrystallized from a mixture of cyclohexane and hexane

Sources & evidence

ORD record
ord-53f3e5c7214146e0a25b2486e453e120
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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