Sodium Bicarbonate → (+/-)-N-[4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]-3,3-diphenyl-2-propenamide

HRID 1739813Notes

Reaction equation

HRID 1739813 reaction equation
[N:1]1([CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:7]2[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Cl[C:21](=[O:36])[CH:22]=[C:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:1]1([CH:6]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:21](=[O:36])[CH:22]=[C:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 112535443,3-Diphenylacryloyl chlorideHCID 141740694-((1H-Imidazol-1-yl)(phenyl)methyl)aniline

Product 1

HCID 15484950(+/-)-N-[4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]-3,3-diphenyl-2-propenamideYield 140.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of intermediate (1-b) (8.92 g) and 1-chloro-3,3-diphenyl-2-propen-1-one (10.42 g) in DCM (100 ml) was stirred at room temperature overnight. The mixture was poured into a 10% NaHCO3 -solution. This mixture was extracted with DCM and separated. The organic layer was dried (MgSO4), filtered and evaporated, yielding 22.85 g (100%) of (±)-N-[4-[(1H-imidazol-1-yl)phenylmethyl]phenyl]-3,3-diphenyl-2-propenamide (interm. 1-c). The product was used without further purification.

Workup

  1. extractionThis mixture was extracted with DCM
  2. customseparated
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-05a942d7253a4c20a9ff8a76031568b4
Source dataset
uspto-grants-1999_10
Patent number
US05968952

Reaction notes

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