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

HRID 6847

반응식

HRID 6847 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]#[N:11])=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].[C:19](=[S:21])=[S:20].Cl[CH2:23][C:24](=[O:26])[CH3:25].CI>CN(C=O)C>[C:24]([C:25]1[S:20][C:19]([S:21][CH3:13])=[C:9]([C:10]#[N:11])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)(=[O:26])[CH3:23]

참가 물질

7

반응물 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 5225133-(4-Methylphenyl)-3-oxopropanenitrile

생성물 1

HCID 220190295-Acetyl-2-methylsulfanyl-4-(4-methyl-phenyl)-thiophene-3-carbonitrile

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

3-(4-Methyl-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 minutes. A solution of 1-chloro-propan-2-one (1.0 equivalent, 5 mmol) in DMF (5 mL) was added. After 1 hour, a solution of MeI (1.1 equivalents, 5.5 mmol) in DMF (2 mL) was added in a dropwise fashion. After 30 minutes, the mixture was poured onto water and the resulting mixture was stirred vigorously for 12–16 hours to afford a suspension of the desired product. The crude product was isolated by filtration.

후처리

  1. stirringthe resulting mixture stirred at room temperature for an additional 10 minutes
  2. waitAfter 1 hour
  3. waitAfter 30 minutes
  4. additionthe mixture was poured onto water
  5. stirringthe resulting mixture was stirred vigorously for 12–16 hours
  6. customto afford

출처 및 근거

ORD 기록
ord-d5067be8faaa479d8cc0710e9fd56529
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084159B2

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