Tetrahydrofuran → HCID 12898690, compound

HRID 1680683Notes

Reaction equation

HRID 1680683 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.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.O1C2C=CC=CC=2N=C1>O>[F:24][C:23]([F:25])([F:26])[C:20]1[CH:21]=[CH:22][C:17]([NH:16][C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 9228BenzoxazoleHCID 99644-(Trifluoromethyl)anilineHCID 119862-Chlorobenzoxazole

Product 1

HCID 12898690HCID 12898690, 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 16.1 g. (0.1 mole) of p-aminobenzotrifluoride 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. Then the reaction mixture was cooled to about 25° C., and about 500 ml. of water was added. The tetrahydrofuran solvent was removed by distillation under vacuum, leaving an aqueous slurry of the reaction product. The solids were filtered off and dried. The dried residue was dissolved in a minimum amount of warm benzene. Then about 200 ml. of hexane was added to the benzene solution to crystallize the reaction product. The crystals were filtered off and dried, yielding 19.2 g. of 2-[4-trifluoromethyl)anilino]benzoxazole having a melting point of 180°-182° 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. customleaving an aqueous slurry of the reaction product
  6. filtrationThe solids were filtered off
  7. customdried
  8. dissolutionThe dried residue was dissolved in a minimum amount of warm benzene
  9. additionof hexane was added to the benzene solution
  10. customto crystallize the reaction product
  11. filtrationThe crystals were filtered off
  12. customdried
  13. customyielding 19.2 g

Sources & evidence

ORD record
ord-13e97a191f6449d1a90d1b725ead0253
Source dataset
uspto-grants-1981_06
Patent number
US04275210

Reaction notes

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