Tetrahydrofuran → HCID 718893, compound

HRID 372023Notes

Reaction equation

HRID 372023 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.O1CCCC1.[F:16][C:17]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:18]=1[NH2:19]>O>[F:16][C:17]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:18]=1[NH:19][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 97092,4-DifluoroanilineHCID 119862-Chlorobenzoxazole

Product 1

HCID 718893HCID 718893, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 15.4 g. (0.1 mole) of 2-chlorobenzoxazole in 200 ml. of tetrahydrofuran was added dropwise a solution of 12.9 g. (0.1 mole) of 2,4-difluoroaniline in 100 ml. of tetrahydrofuran with vigorous agitation. Following the addition, the reaction mixture was heated on a steam bath under reflux for 16 hours. The reaction mixture was cooled to about 25° C., and about 500 ml. of water added thereto. The tetrahydrofuran solvent was removed by distillation under vacuum. The precipitate which formed in the aqueous medium was removed by filtration and dried. The dried precipitate was dissolved in a minimum amount of warm benzene. About 200 ml. of hexane was added to the benzene solution to effect crystallization of the reaction product. The precipitate was filtered off and dried, yielding 18.3 g. of 2-(2,4-difluoroaniline)benzoxazole having a melting point of 115°-117° C.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was heated on a steam bath
  3. temperatureunder reflux for 16 hours
  4. customThe tetrahydrofuran solvent was removed by distillation under vacuum
  5. customThe precipitate which formed in the aqueous medium
  6. customwas removed by filtration
  7. customdried
  8. dissolutionThe dried precipitate was dissolved in a minimum amount of warm benzene
  9. additionof hexane was added to the benzene solution
  10. customcrystallization of the reaction product
  11. filtrationThe precipitate was filtered off
  12. customdried
  13. customyielding 18.3 g

Sources & evidence

ORD record
ord-f6bb9f5b25774075808694386f436a43
Source dataset
uspto-grants-1978_05
Patent number
US04088770

Reaction notes

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