Tetrahydrofuran → HCID 12898690, compound

HRID 372024Notes

Reaction equation

HRID 372024 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-02de88c680d9410a9813bc21e0435fef
Source dataset
uspto-grants-1978_05
Patent number
US04088770

Reaction notes

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