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

HRID 6847

反応式

HRID 6847 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5067be8faaa479d8cc0710e9fd56529
出典データセット
uspto-grants-2006_08
特許番号
US07084159B2

関連ノート

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