Water → HCID 681880, compound

HRID 406316Notes

Reaction equation

HRID 406316 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].N1C=CC=CC=1.Cl[C:19]([O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20].O>O1CCCC1>[F:11][C:8]([F:9])([F:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:19](=[O:20])[O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 69222-(Trifluoromethyl)anilineHCID 15891Phenyl chloroformate

Product 1

HCID 681880HCID 681880, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Aminobenzotrifluoride (5 mL) and pyridine (6.44 mL) were dissolved in tetrahydrofuran (100 mL), and phenyl chloroformate (5.5 mL) was added dropwise under ice-cooling. After dropwise addition of the reagent, the mixture was brought back to room temperature and stirred for 4.5 hours. Water was added to the reaction solution and the mixture was concentrated under reduced pressure, followed by extraction with ethyl acetate. The resulting organic layer was washed with 2 N hydrochloric acid and brine and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration, and then the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (12.1 g). The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. additionAfter dropwise addition of the reagent
  3. customwas brought back to room temperature
  4. concentrationthe mixture was concentrated under reduced pressure
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe resulting organic layer was washed with 2 N hydrochloric acid and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe drying agent was separated by filtration
  9. concentrationthe organic layer was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63b4749950404b37bb6d83f8f46c054a
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

Loading…