Acetone → Methanone, (2,4-diphenyl-1H-pyrrol-3-yl)phenyl-

HRID 1975773Notes

Reaction equation

HRID 1975773 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([CH2:18][C:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)=O>C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Ni+2].O>[C:20]1([C:19]2[NH:8][CH:9]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:18]=2[C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 8433DibenzoylmethaneHCID 190986582-Phenylazirine

Product 1

HCID 3741094Methanone, (2,4-diphenyl-1H-pyrrol-3-yl)phenyl-

Reagents, catalysts & solvents 2

HCID 9834912Nickel(II) acetylacetonateCatalystHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

With stirring, 3.0 g of 2-phenylazirine are added dropwise to a solution of 5.6 g of dibenzoylmethane, 10 ml of acetone and 0.1 g of nickel acetylacetonate at 50° C. The mixture is then heated at reflux for 30 minutes, cooled to 20° C., and 25 ml of water are added. The precipitated crystals are filtered with suction, washed with water, and dried to constant weight.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 30 minutes
  3. filtrationThe precipitated crystals are filtered with suction
  4. washwashed with water
  5. customdried to constant weight

Sources & evidence

ORD record
ord-bb623bd255a54628bf38e3b490d6928e
Source dataset
uspto-grants-1994_02
Patent number
US05288776

Reaction notes

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