Sodium Hydroxide → 2-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole

HRID 1721368Notes

Reaction equation

HRID 1721368 reaction equation
Cl.[CH3:2][C:3]1[N+:4]([O-])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8].P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:22][CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[O:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 11150543HCID 11150543, compound

Product 1

HCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazoleYield 28.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
5 °C

Procedure

In to a 5° C. solution of 4,5-dimethyl-2-(4-trifluoromethyl-phenyl)-oxazole N-oxide hydrochloride (113.71 g, 387.5 mmol) in CHCl3 (560 ml), was added phosphorus oxychloride (39.4 ml, 422.4 mmol) in CHCl3, dropwise over 15 min. The reaction was refluxed for 2.5 h, then cooled to 5° C., poured into ice water, and basified with NaOH (1N). The organic layer was dried over MgSO4. Evaporation and recrystallization from ether/hexane, gave a yellow solid (30.0 g, 28% yield, mp 84°-85° C.).

Workup

  1. temperatureThe reaction was refluxed for 2.5 h
  2. dry with materialThe organic layer was dried over MgSO4
  3. customEvaporation and recrystallization from ether/hexane

Sources & evidence

ORD record
ord-21da93fee7a346f08f960ad3c984909c
Source dataset
uspto-grants-1996_04
Patent number
US05510360

Reaction notes

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