Sodium hydride → N,N-dimethyl3, 3-di(4-biphenylyl) acrylamide

HRID 1580520Notes

Reaction equation

HRID 1580520 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)=O)=[CH:3][CH:2]=1.C(OP([CH2:35][C:36](=[O:40])[N:37]([CH3:39])[CH3:38])(=O)OCC)C.[H-].[Na+]>C1C=CC=CC=1>[CH3:39][N:37]([CH3:38])[C:36](=[O:40])[CH:35]=[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)[C:4]1[CH:3]=[CH:2][C:1]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2284534,4'-DiphenylbenzophenoneHCID 11127903diethyl N,N-dimethylcarbamoylmethylphosphonate

Product 1

HCID 53672088N,N-dimethyl3, 3-di(4-biphenylyl) acrylamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Di-4-biphenylyl ketone (6.68 g.) was added to a mixture of N,N-Di-methylcarbamoylmethyl phosphonic acid diethyl ester (C.A. 65, 615 g. 1966) (4.46 g.), sodium hydride (60%) (0.8 g.) and benzene (400 ml.). The mixture was boiled under reflux for sixty hours. The benzene layer, decanted and evaporated, gave an oil, from which, by column chromatography on silica gel MFC in benzene and elution by ethyl acetate, was isolated N,N-dimethyl3, 3-di(4-biphenylyl) acrylamide, m.p. 121°C after recrystallisation from light petroleum (b.p. 80°-100°C). This, reduced with lithium aluminium hydride in ether/tetrahydrofuran at -30°C, gave 1,1-di(4-biphenylyl) -3 -dimethylaminoprop-1-ene identical with that described in Example 1 .

Workup

  1. temperatureunder reflux for sixty hours
  2. customThe benzene layer, decanted
  3. customevaporated
  4. customgave an oil
  5. washfrom which, by column chromatography on silica gel MFC in benzene and elution by ethyl acetate

Sources & evidence

ORD record
ord-146f7140bc70421e92ca345a6485d145
Source dataset
uspto-grants-1976_01
Patent number
US03932663

Reaction notes

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