Dimethyl Sulfoxide → HCID 21783881、化合物

HRID 2392520ノート

反応式

HRID 2392520 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 21783881HCID 21783881、化合物収率 25.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2610f2ebf20a4bafbb6952adc369e5ec
出典データセット
uspto-grants-1998_09
特許番号
US05801008

反応ノート

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