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

反応式

HRID 258194 の反応式
[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

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3d85d073429848d7a0bae10a9d71d26a
出典データセット
uspto-grants-1993_11
特許番号
US05264577

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