Dimethyl Sulfoxide → HCID 21860269, compound

HRID 2392522Notes

Reaction equation

HRID 2392522 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]([C:27]2[S:28][CH:29]=[CH:30][CH:31]=2)[C:17]=1[C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:33][C:32]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]([C:27]3[S:28][CH:29]=[CH:30][CH:31]=3)[C:17]=12

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 11430Potassium CarbonateHCID 12980Dimethyl acetylenedicarboxylateHCID 21860261HCID 21860261, compound

Product 1

HCID 21860269HCID 21860269, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A dimethylsulfoxide (20 ml) solution of 10.0 g (70 mmol) of dimethyl acetylenedicarboxylate was dropwise added to a mixture comprised of 2.66 g (10 mmol) of 5-amino-1-phenyl-3-(thiophen-2-yl)pyrazole-4-carbonitrile, 27.6 g (200 mmol) of anhydrous potassium carbonate and 300 ml of dimethylsulfoxide, while cooling with ice, over a period of 30 minutes, 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 by filtration, dried in air and added to 20 ml of methanol. The white crystals thus formed were taken out by filtration and recrystallized from methanol to obtain 3.50 g of the entitled product as colorless crystals having a melting point of 178° to 180° C.

Workup

  1. temperaturewhile cooling with ice, over a period of 30 minutes
  2. customDuring the stirring, the reaction liquid
  3. customAfter the reaction
  4. customthe liquid reaction mixture
  5. stirringstirred for 30 minutes at room temperature
  6. customThe blackish brown solid thus precipitated
  7. filtrationwas taken out by filtration
  8. customdried in air
  9. additionadded to 20 ml of methanol
  10. customThe white crystals thus formed
  11. filtrationwere taken out by filtration
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-435a97f9d47d4e9c8e0d4f76c7d1ec59
Source dataset
uspto-grants-1998_09
Patent number
US05801008

Reaction notes

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