HCID 21318139, compound → HCID 21318144, compound

HRID 263066Notes

Reaction equation

HRID 263066 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([NH2:20])=O)=[CH:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5]>C(Cl)(Cl)Cl>[F:22][C:2]([F:1])([F:21])[C:3]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]#[N:20])=[CH:12]2)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

3

Reactant 1

HCID 21318139HCID 21318139, compound

Product 1

HCID 21318144HCID 21318144, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 8.50 g. (0.026 mol) of 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carboxamide in 100 ml. of chloroform and 100 ml. of an ether-chloroform solution of polyphosphate ester was heated under reflux for 45 minutes and concentrated under vacuum. The residue was mixed with ether and water and made basic with sodium bicarbonate. The ether layer was then dried and concentrated, and the residue was mixed with dichloromethane. Filtration removed a little starting material and concentration gave several crops of crude 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carbonitrile. The mother liquors were absorbed on silica gel from benzene solution. Elution with 0-10% ether in dichloromethane gave further 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carbonitrile. Recrystallization of the combined material from dichloromethane gave 5.60 g. (70%) of 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carbonitrile as colorless crystals, m.p. 183°-185°. The analytical sample had m.p. 181°-184°.

Workup

  1. temperatureunder reflux for 45 minutes
  2. concentrationconcentrated under vacuum
  3. additionThe residue was mixed with ether and water
  4. dry with materialThe ether layer was then dried
  5. concentrationconcentrated
  6. additionthe residue was mixed with dichloromethane
  7. filtrationFiltration
  8. customremoved
  9. concentrationmaterial and concentration
  10. customgave several crops of crude 5-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]indole-2-carbonitrile
  11. customThe mother liquors were absorbed on silica gel from benzene solution
  12. washElution with 0-10% ether in dichloromethane

Sources & evidence

ORD record
ord-bd3adabe7c184b7e8608a8e192b6de3b
Source dataset
uspto-grants-1979_05
Patent number
US04156016

Reaction notes

Loading…