Water → HCID 21930273, compound

HRID 1243644Notes

Reaction equation

HRID 1243644 reaction equation
[CH3:1][NH:2][NH2:3].C(OCC)(=O)C.O.[CH:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24](/[CH:26]=[CH:27]/[C:28]3[O:32][CH:31]=[CH:30][CH:29]=3)=O)=[CH:20][CH:19]=2)=[CH:13][CH:12]=1>CS(C)=O>[O:32]1[CH:31]=[CH:30][CH:29]=[C:28]1[C:27]1[N:2]([CH3:1])[N:3]=[C:24]([C:21]2[CH:22]=[CH:23][C:18]([O:17][C:14]3[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=3)=[CH:19][CH:20]=2)[CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6061MethylhydrazineHCID 8857Ethyl AcetateHCID 5761334HCID 5761334, compound

Product 1

HCID 21930273HCID 21930273, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

In an open vial, 3-furan-2-yl-1-(4-phenoxy-phenyl)-propenone (0.4 g) was dissolved in dimethylsulfoxide (10 mL). Methylhydrazine (1.0 g) was added and the reaction mixture was heated to 85° C. for 3 days. The reaction mixture was cooled to room temperature and ethyl acetate (100 mL) and water (50 mL) were added. The organic layer was washed twice with water (25 mL), then separated and dried over sodium sulfate. The solvent was removed after filtering away the drying agent. Purification by column chromatography (silica, eluted with ethyl acetate-hexanes, 1:9) gave the desired pyrazole in moderate yield (0.1 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic layer was washed twice with water (25 mL)
  3. customseparated
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. filtrationafter filtering away the drying agent
  7. customPurification
  8. washby column chromatography (silica, eluted with ethyl acetate-hexanes, 1:9)

Sources & evidence

ORD record
ord-0800e8376dc8413bb7062a8659dd05b3
Source dataset
uspto-grants-2006_10
Patent number
US07119120B2

Reaction notes

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