Hydrochloric Acid → 959139-51-6

HRID 660887Notes

Reaction equation

HRID 660887 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[C:6]([CH:9]=1)[C:7]#[N:8].Cl>C1COCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:11])([F:12])[F:13])=[C:6]([CH2:7][NH2:8])[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 177508345-Chloro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 57455738959139-51-6

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

29.2 ml of borane-THF complex (29.2 mmol) are slowly added dropwise under argon to an ice-cooled solution of 5-chloro-2-(trifluoromethyl)benzonitrile (1.50 g, 7.3 mmol) in 45 ml of anhydrous THF. After the end of the addition, the mixture is heated under reflux for 1 hr, then stirred overnight at RT with cooling. 30 ml of 1 N hydrochloric acid are then added dropwise with ice-cooling. The THF is removed on the rotary evaporator. The precipitated solid is filtered off and discarded. The filtrate is diluted with water and extracted twice with dichloromethane. These organic phases are also discarded. The acidic aqueous phase is adjusted to pH 14 with 1 N aqueous sodium hydroxide and extracted three times with dichloromethane. The combined organic phases are dried over sodium sulphate and freed of solvent on the rotary evaporator. The residue is taken up in 20 ml diethyl ether and treated with 3 ml of a 4 N solution of hydrogen chloride in dioxan, during which the product precipitates. The solvent is completely removed on the rotary evaporator, then in high vacuum. 1.89 g (99% of theory) of the title compound are isolated.

Workup

  1. additionAfter the end of the addition
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 1 hr
  4. temperaturewith cooling
  5. temperaturecooling
  6. customThe THF is removed on the rotary evaporator
  7. filtrationThe precipitated solid is filtered off
  8. additionThe filtrate is diluted with water
  9. extractionextracted twice with dichloromethane
  10. extractionextracted three times with dichloromethane
  11. dry with materialThe combined organic phases are dried over sodium sulphate
  12. customfreed of solvent on the rotary evaporator
  13. additiontreated with 3 ml of a 4 N solution of hydrogen chloride in dioxan, during which the product
  14. customprecipitates
  15. customThe solvent is completely removed on the rotary evaporator

Sources & evidence

ORD record
ord-b8b76c81ba504a78b1f909a10750dd1f
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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