2-Chlorobenzoxazole → HCID 12898688, compound

HRID 372022Notes

Reaction equation

HRID 372022 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].Cl[C:14]1[O:15][C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=1>O1CCCC1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:14]2[O:15][C:16]3[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 753774-Fluoro-3-(trifluoromethyl)aniline

Product 1

HCID 12898688HCID 12898688, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 17.9 g. (0.1 mole) of 4-fluoro-3-(trifluoromethyl)aniline in 200 ml. of tetrahydrofuran was added dropwise 15.4 g. (0.1 mole) of 2-chlorobenzoxazole in 150 ml. of tetrahydrofuran with vigorous agitation. Following the addition, the reaction mixture was heated on a steam bath under reflux for 16 hours. Then the tetrahydrofuran solvent was removed by distillation under vacuum, and 100 ml. of water was added to the residue. The residue was an oily liquid which solidified on the addition of the water. The residue was removed by filtration and dried in vacuo. The dried residue was dissolved in a minimum amount of warm acetone, and about 200 ml. of water was added to the solution, resulting in the crystallization of the reaction product. The precipitate was filtered and dried and 24.5 g. of 2-[4-fluoro-3-(trifluoromethyl)anilino]benzoxazole having a melting point of 190°-191° C. was recovered.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was heated on a steam bath
  3. temperatureunder reflux for 16 hours
  4. customThen the tetrahydrofuran solvent was removed by distillation under vacuum, and 100 ml
  5. additionof water was added to the residue
  6. additionsolidified on the addition of the water
  7. customThe residue was removed by filtration
  8. customdried in vacuo
  9. dissolutionThe dried residue was dissolved in a minimum amount of warm acetone, and about 200 ml
  10. additionof water was added to the solution
  11. customresulting in the crystallization of the reaction product
  12. filtrationThe precipitate was filtered
  13. customdried
  14. customof 2-[4-fluoro-3-(trifluoromethyl)anilino]benzoxazole having a melting point of 190°-191° C. was recovered

Sources & evidence

ORD record
ord-748186a749ab4d2b919203a3bf6b7e30
Source dataset
uspto-grants-1978_05
Patent number
US04088770

Reaction notes

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