Phosphorus oxychloride → 2-Chloro-6-{[1-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)ethylidene]amino}benzonitrile

HRID 540312

반응식

HRID 540312 반응식
P(Cl)(Cl)(Cl)=O.[CH2:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][CH2:8][N:7]1[C:17](=O)[CH3:18].[NH2:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:22]=1[C:23]#[N:24].C(=O)(O)[O-].[Na+]>ClCCl.O>[Cl:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:21]([N:20]=[C:17]([N:7]2[CH2:8][CH2:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH2:6]2)[CH3:18])[C:22]=1[C:23]#[N:24]

참가 물질

7

반응물 4

HCID 24813Phosphorus oxychlorideHCID 810562-Amino-6-chlorobenzonitrileHCID 516892Sodium BicarbonateHCID 104651101-(1,3,4,5-Tetrahydro-2H-2-benzazepin-2-yl)ethanone

생성물 1

HCID 712545892-Chloro-6-{[1-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)ethylidene]amino}benzonitrile수율 63.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

Phosphorus oxychloride (2.93 mL, 32.0 mmol) was added to a stirred solution of 1-(1,3,4,5-tetrahydro-2H-2-benzazepin-2-yl)ethanone (5.5 g, 29.0 mmol) in dry dichloromethane (100 mL) at 10° C. After that, the mixture was stirred for 20 minutes at room temperature. Then a solution of 2-amino-6-chloro-benzonitrile (4.43 g, 29.0 mmol) in dry dichloromethane (40 mL) was added and the resulting suspension was heated under reflux for 24 hours. After the reaction mixture was cooled to room temperature, water (50 mL) was added followed by saturated sodium bicarbonate to pH 8. The organic layer was separated and the aqueous was extracted with dichloromethane (100 mL). The organic fraction was washed with brine and dried over sodium sulfate, and then evaporated in vacuo to give a residue which was precipitated in ether. The solid was collected by filtration and dried in vacuo to give 6 g of product as a brown powder (yield was 63.7%). It was used in the next step without further purification. MS obsd. (ESI+) [(M+H)+] 324.

후처리

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with dichloromethane (100 mL)
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customto give a residue which
  10. customwas precipitated in ether
  11. filtrationThe solid was collected by filtration
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-1a12b80a46b04bebbaefe099bf976c4b
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871756B2

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