5H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro- → Ethyl alpha-[(diphenylmethylene)amino]-10,11,dihydro-5H-dibenzo[a,d]cycloheptene-5-acetate

HRID 258194

반응식

HRID 258194 반응식
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:21]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29](Cl)[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22]1.[OH-].[Na+]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)C>[C:1]1([C:7](=[N:8][CH:9]([CH:29]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22][CH2:21][C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]2=3)[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

8

반응물 3

HCID 145875H-Dibenzo(a,d)cycloheptene, 10,11-dihydro-5-chloro-HCID 14798Sodium HydroxideHCID 319508Ethyl 2-(diphenylmethyleneamino)acetate

생성물 1

HCID 19385932Ethyl alpha-[(diphenylmethylene)amino]-10,11,dihydro-5H-dibenzo[a,d]cycloheptene-5-acetate수율 101.5%

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

Ethyl N-(diphenylmethylene)glycinate (12 g, 45 mmol) and 5-chlorodibenzosuberane (12.32 g, 54 mmol) are dissolved in 250 mL of dichloromethane, tetrabutylammonium bromide (17.6 g, 55 mmol) and 47 mL of 50% sodium hydroxide solution are added and the mixture is mechanically stirred at room temperature for 4 hours. Then it is diluted with 75 mL of dichloromethane and water and the layers are separated. The organic layer is washed with water, dried over magnesium sulfate, filtered, and stripped under vacuum to give a brown orange oil. The oil is taken up in 250 mL of diethyl ether and 100 mL of water. The diethyl ether solution is additionally washed with water, dried (magnesium sulfate), and stripped to give a clear red-orange sticky oil residue (~21 g) which is used in the next step without purification.

후처리

  1. customthe layers are separated
  2. washThe organic layer is washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customto give a brown orange oil
  6. washThe diethyl ether solution is additionally washed with water
  7. dry with materialdried (magnesium sulfate)

출처 및 근거

ORD 기록
ord-3d85d073429848d7a0bae10a9d71d26a
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264577

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