Ethanol → HCID 18463809, compound

HRID 2288899Notes

Reaction equation

HRID 2288899 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2N=C(C(F)(F)F)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([OH:27])C.O.OOS([O-])=O.[K+]>C1COCC1>[OH:11][CH:12]([C:13]1[CH:18]=[CH:17][C:16]([S:19][CH3:20])=[CH:15][CH:14]=1)[C:8]([C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:27]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 18701861HCID 18701861, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 18463809HCID 18463809, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Methylphenyl)-5-(4-methylthiophenyl)-2-trifluoromethyloxazole from Step 2 (350 mg, 1.0 mmol) was dissolved in THF (20 mL), ethanol (20 mL) and water (20 mL). Oxone® (1.2 g, 2 mmol) was added and the reaction stirred for 3 hours. The reaction mixture was filtered and concentrated to dryness. The residue was dissolved in ethyl acetate (200 mL), washed with water, NaHCO3 and brine, dried and concentrated to yield a white crystalline product (350 mg) which was recrystallized from ethanol and water to yield 4-(4-methylphenyl)-5-(4-methylsulfonylphenyl)-2-trifluoromethyl-oxazole (300 mg, 79%): mp 141-142° C. Anal. Calc'd. for C18H14NO3SF3 : C, 56.69; H, 3.70; N, 3.67. Found: C, 56.47; H, 3.79; N, 3.57.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated to dryness
  3. dissolutionThe residue was dissolved in ethyl acetate (200 mL)
  4. washwashed with water, NaHCO3 and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5e06210fa48e48fc9c8de3cbddba887e
Source dataset
uspto-grants-2000_07
Patent number
US06090834

Reaction notes

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