2-Hydrazinylidene-1,2-diphenylethan-1-one → HCID 12688534, compound

HRID 1732649Notes

Reaction equation

HRID 1732649 reaction equation
[C:1]1([C:7](=[N:16][NH2:17])[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18]1([S:24]([CH2:27][C:28](OCC)=[O:29])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[O-]CC.[Na+]>C(O)C>[C:18]1([S:24]([C:27]2[C:28](=[O:29])[NH:17][N:16]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:25])=[O:26])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 792892-Hydrazinylidene-1,2-diphenylethan-1-oneHCID 82078Ethyl (phenylsulphonyl)acetateHCID 2723922Sodium ethoxide

Product 1

HCID 12688534HCID 12688534, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Benzilmonohydrazone (20.3 g) and ethyl α-phenylsulfonylacetate (22.8 g) were charged to a dry reaction flask in absolute ethanol (250 ml). With stirring, sodium ethoxide (6.8 g) was added portionwise When addition was complete, the reaction was heated to reflux for 12 hours. During this time, a 10 percent excess (2.3 g) of the ester was added. The cooled solution was quenched in an equal volume of water and concentrated HCl was added to precipitate a solid. The product was filtered from the cold mixture and recrystallized from ethanol to obtain the title compound as a white solid (34 percent yield), m.p. 254°-256° C.

Workup

  1. additionWhen addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 12 hours
  4. customThe cooled solution was quenched in an equal volume of water and concentrated HCl
  5. additionwas added
  6. customto precipitate a solid
  7. filtrationThe product was filtered from the cold mixture
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a19b5ef609e84c208cffcf290743f1b9
Source dataset
uspto-grants-1980_12
Patent number
US04238490

Reaction notes

Loading…