2-Chlorobenzoxazole → N-[2-Fluoro-5-(trifluoromethyl)phenyl]-2-benzoxazolamine

HRID 372021Notes

Reaction equation

HRID 372021 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[F:11][C:12]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:13]=1[NH2:14]>O1CCCC1>[F:11][C:12]1[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:13]=1[NH:14][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 1363492-Fluoro-5-(trifluoromethyl)aniline

Product 1

HCID 12898687N-[2-Fluoro-5-(trifluoromethyl)phenyl]-2-benzoxazolamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-chlorobenzoxazole (15.4 g., 0.1 mole) in 150 ml. of tetrahydrofuran was added dropwise to a solution of 2-fluoro-5-(trifluoromethyl)aniline in 200 ml. of refluxing tetrahydrofuran. Reflux of the reaction mixture was continued on a steam bath for 16 hours. The tetrahydrofuran solvent was then removed by distillation under vacuum. The oily residue was solidified by addition of approximately 100 ml. of water. The solid material was separated by filtration and was recrystallized from an acetone-water solvent mixture to give 2-[2-fluoro-5-(trifluoromethyl)anilino]benzoxazole having a melting point of 164°-165° C.

Workup

  1. temperatureReflux of the reaction mixture
  2. customThe tetrahydrofuran solvent was then removed by distillation under vacuum
  3. additionThe oily residue was solidified by addition of approximately 100 ml
  4. customThe solid material was separated by filtration
  5. customwas recrystallized from an acetone-water solvent mixture

Sources & evidence

ORD record
ord-57fa4c3b142c4447ad4c14f1e776b2aa
Source dataset
uspto-grants-1978_05
Patent number
US04088770

Reaction notes

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