Methanol → HCID 13754490, compound

HRID 1249559Notes

Reaction equation

HRID 1249559 reaction equation
[CH3:1][CH:2]([C:4]1[S:8][C:7]([C:9]([C:15]([F:18])([F:17])[F:16])([C:11]([F:14])([F:13])[F:12])[OH:10])=[N:6][C:5]=1[C:19]1[CH:24]=[CH:23][C:22](SC)=[CH:21][CH:20]=1)[CH3:3].O[O:28][S:29]([O-:31])=O.[K+].S(OOS([O-])(=O)=O)(O)(=O)=O.[K+].[CH3:44]O>>[CH3:3][CH:2]([C:4]1[S:8][C:7]([C:9]([C:15]([F:17])([F:16])[F:18])([C:11]([F:13])([F:14])[F:12])[OH:10])=[N:6][C:5]=1[C:19]1[CH:20]=[CH:21][C:22]([S:29]([CH3:44])(=[O:31])=[O:28])=[CH:23][CH:24]=1)[CH3:1]

Participants

5

Reactant 4

HCID 887MethanolHCID 23690007Potassium hydrogen persulfateHCID 23707502Potassium hydroxy sulfiteHCID 54299138HCID 54299138, compound

Product 1

HCID 13754490HCID 13754490, compound

Conditions

Temperature
25 °C

Procedure

To a solution of 5.90 g (14.2 mmol) of 5-(1-methylethyl)-4-(4-methylthiophenyl)-α,α-bis(trifluoromethyl)thiazole-2-methanol in 200 ml of methanol at 25° C. was added 21.3 g (34.7 mmol) of Oxone® (potassium hydrogen persulfate) and the resulting suspension was stirred at 25° C. for 3 hours. The suspension was filtered, and the filtrate concentrated in vacuo. The residue was dissolved in ethyl acetate; and the solution was washed with distilled water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product was recrystallized from n-butyl chloride to provide 3.34 g of 5-(1-methylethyl)-4-(4-methylsulfonylphenyl)-α,α-bis(trifluoromethyl)thiazole-2-methanol as a yellow crystalline solid, m.p. 122°-123° C.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washand the solution was washed with distilled water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was recrystallized from n-butyl chloride

Sources & evidence

ORD record
ord-9ac9cdc2f09044ae94a3e9ff7051824c
Source dataset
uspto-grants-1986_12
Patent number
US04632930

Reaction notes

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