Chlorodiphenylmethane → Methyl Z-4-[[5-[[3-[(1,1'-biphenyl)-4-ylmethyl]-1-butyl-2,5-dioxo-4-imidazolidinylidene]methyl]-2-butyl-1H-imidazol-1-yl]methyl]benzoate

HRID 1648527Notes

Reaction equation

HRID 1648527 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[C:7](/[CH:10]=[C:11]2\[NH:12][C:13](=[O:21])[N:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15]\2=[O:16])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[C:33]([O-])([O-])=O.[K+].[K+].[C:39]1([CH:45](Cl)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:44]=[CH:43][CH:42]=[CH:41]C=1>CN(C=O)C>[C:46]1([C:45]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:39]=2)[CH:47]=[CH:48][C:49]([CH2:33][N:12]2[C:13](=[O:21])[N:14]([CH2:17][CH2:18][CH2:19][CH3:20])[C:15](=[O:16])/[C:11]/2=[CH:10]/[C:7]2[N:6]([CH2:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=3)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][CH:8]=2)=[CH:50][CH:51]=1

Participants

5

Reactant 3

HCID 7035ChlorodiphenylmethaneHCID 11430Potassium CarbonateHCID 11743857Methyl Z-4-[[2-butyl-5-[(1-butyl-2,5-dioxo-4-imidazolidinylidene)methyl]-1H-imidazol-1-yl]methyl]benzoate

Product 1

HCID 19919870Methyl Z-4-[[5-[[3-[(1,1'-biphenyl)-4-ylmethyl]-1-butyl-2,5-dioxo-4-imidazolidinylidene]methyl]-2-butyl-1H-imidazol-1-yl]methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl Z-4-[[2-butyl-5-[[1-butyl-2,5-dioxo-4-imidazolidinylidene]methyl]-1H-imidazol-1-yl]methyl]benzoate (0.438 g, 1.00 mmol) in DMF (10 mL) is added K2CO3 (0.42 g, 3.00 mmol). After stirring for 5 minutes diphenylmethyl chloride (0.210 g, 1.00 mmol) is added. The mixture is stirred for 16 hours, filtered, and evaporated in vacuo. The gum is dissolved in ethyl acetate and washed with water, brine and dried over MgSO4. Chromatography eluting with (50-100)% ethyl acetate in hexane, evaporation in vacuo affords a foam.

Workup

  1. additionis added
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. dissolutionThe gum is dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. washChromatography eluting with (50-100)% ethyl acetate in hexane, evaporation in vacuo
  8. customaffords a foam

Sources & evidence

ORD record
ord-8d0ed006c2be4f96ad1fd3b6d5e76836
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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