Methyl iodide → 4-Acetyl-3-methyl-5-(methylthio)thiophene-2-carbonitrile

HRID 6848

반응식

HRID 6848 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].[C:8]([O-])([O-])=O.[K+].[K+].[C:14](=[S:16])=[S:15].Cl[CH2:18][C:19]#[N:20].CI>CN(C=O)C.O>[C:2]([C:3]1[C:4]([CH3:5])=[C:18]([C:19]#[N:20])[S:15][C:14]=1[S:16][CH3:8])(=[O:7])[CH3:1]

참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 31261Acetylacetone

생성물 1

HCID 28201864-Acetyl-3-methyl-5-(methylthio)thiophene-2-carbonitrile

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a slurry of 2,4-pentanedione (20 mmol) and K2CO3 (3 equivalents, 60 mmol) in DMF (10 mL) was added CS2 (1.2 equivalents, 24 mmol) and the resulting mixture stirred for 10 minutes. The mixture was cooled to 0° C. then chloroacetonitrile (1.0 equivalent, 20 mmol) was added and the reaction stirred 1 hour then warmed to room temperature and stirred for an additional 2 hours. The reaction mixture was again cooled to 0° C. and methyl iodide (1.05 equivalents, 22 mmol) was added slowly. The resulting mixture was warmed to room temperature. After 12 hours, water was added and the resulting suspension was stirred overnight. The desired product was isolated by filtration after washing with water.

후처리

  1. stirringthe reaction stirred 1 hour
  2. temperaturethen warmed to room temperature
  3. stirringstirred for an additional 2 hours
  4. temperatureThe reaction mixture was again cooled to 0° C.
  5. temperatureThe resulting mixture was warmed to room temperature
  6. waitAfter 12 hours
  7. stirringthe resulting suspension was stirred overnight

출처 및 근거

ORD 기록
ord-fab1cf601eeb4f96bf3c58d1ce626549
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084159B2

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