Potassium Iodide → 1-(2-Dimethylaminoethyl)-2-{[[4-(2-furylmethylthio)-3-methyl-2-pyridinyl]methyl]-thio}-benzimidazole

HRID 1871943ノート

反応式

HRID 1871943 の反応式
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)[C:9]=1[CH3:25].Cl.[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[CH3:27][N:28]([CH3:32])[CH2:29][CH2:30][N:20]1[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[N:17]=[C:16]1[S:15][CH2:14][C:10]1[C:9]([CH3:25])=[C:8]([S:7][CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[CH:13]=[CH:12][N:11]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 97993662-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazoleHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

生成物 1

HCID 186900181-(2-Dimethylaminoethyl)-2-{[[4-(2-furylmethylthio)-3-methyl-2-pyridinyl]methyl]-thio}-benzimidazole収率 74%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-{[[4-(2-Furylmethylthio)-3-methyl-2-pyridinyl]methyl]thio}-1H-benzimidazole is stirred with 2-dimethylamino-ethyl chloride hydrochloride (1.5 equivalents), potassium carbonate (5 equivalents) and potassium iodide (0.05 equivalents) in acetonitrile at 100° C. for 24 h, the mixture is filtered, the filtrate is concentrated on a rotary evaporator, water is added to the residue and the mixture is extracted with methylene chloride. The combined organic phases are washed with water, dried and concentrated. The residue is crystallized from methylene chloride/diisopropyl ether. The title compound is obtained as a colorless powder; m.p. 87-89° C.; yield: 74% of theory.

後処理

  1. filtrationthe mixture is filtered
  2. concentrationthe filtrate is concentrated on a rotary evaporator, water
  3. additionis added to the residue
  4. extractionthe mixture is extracted with methylene chloride
  5. washThe combined organic phases are washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe residue is crystallized from methylene chloride/diisopropyl ether

出典と根拠

ORDレコード
ord-c13319dfaea3499f96d5798384213b91
出典データセット
uspto-grants-2000_08
特許番号
US06107312

反応ノート

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