Hydrochloric Acid → (5-Chloro-2-(trifluoromethyl)phenyl)methanamine hydrochloride

HRID 660887ノート

反応式

HRID 660887 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 57455738(5-Chloro-2-(trifluoromethyl)phenyl)methanamine hydrochloride

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8b76c81ba504a78b1f909a10750dd1f
出典データセット
uspto-grants-2011_12
特許番号
US08084481B2

反応ノート

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