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 2399628Notes

Reaction equation

HRID 2399628 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][N:7]=[C:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5].[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:9]1([C:8](=[N:7][CH:6]([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:4]([O:3][CH2:2][CH3:1])=[O:5])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-d424ed98e09d419ea9f8c1c361aff8a3
Source dataset
uspto-grants-1995_09
Patent number
US05449778

Reaction notes

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