Dimethyl Sulfoxide → HCID 21783881, compound

HRID 2392520Notes

Reaction equation

HRID 2392520 reaction equation
CS(C)=O.[C:5]([C:11]([O:13][CH3:14])=[O:12])#[C:6][C:7]([O:9][CH3:10])=[O:8].[NH2:15][C:16]1[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:19]=[C:18]([S:27][CH3:28])[C:17]=1[C:29]#[N:30].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:30][C:29]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:11]([O:13][CH3:14])=[O:12])[N:15]=[C:16]2[N:20]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=[C:18]([S:27][CH3:28])[C:17]=12

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 11430Potassium CarbonateHCID 12980Dimethyl acetylenedicarboxylateHCID 7367765-Amino-3-(methylsulfanyl)-1-phenyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 21783881HCID 21783881, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethylsulfoxide (20 ml) solution of 9.0 g (63 mmol) of dimethyl acetylenedicarboxylate was dropwise added to a mixture comprised of 11.5 g (50 mmol) of 5-amino-3-methylthio-1-phenylpyrazole-4-carbonitrile, 20.8 g (145 mmol) of anhydrous potassium carbonate and 300 ml of dimethylsulfoxide, while stirring and cooling with ice, and then stirred for further 60 hours at room temperature. During the stirring, the reaction liquid was changed from brown to greenish brown. After the reaction, the liquid reaction mixture was poured into 500 ml of water with ice and stirred for 30 minutes at room temperature. The blackish brown solid thus precipitated was taken out, and 20 ml of methanol was added thereto and heated. The white crystals thus formed were taken out by means of filtration under suction and recrystallized from methanol to obtain 4.80 g (12.8 mmol) of the entitled product as colorless, needle-like crystals having a melting point of 120° to 122° C.

Workup

  1. temperaturecooling with ice
  2. stirringstirred for further 60 hours at room temperature
  3. customDuring the stirring, the reaction liquid
  4. customAfter the reaction
  5. customthe liquid reaction mixture
  6. stirringstirred for 30 minutes at room temperature
  7. customThe blackish brown solid thus precipitated
  8. addition20 ml of methanol was added
  9. temperatureheated
  10. customThe white crystals thus formed
  11. filtrationwere taken out by means of filtration under suction
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-2610f2ebf20a4bafbb6952adc369e5ec
Source dataset
uspto-grants-1998_09
Patent number
US05801008

Reaction notes

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