Water → N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1H-indole-3-ethanamine

HRID 2419564ノート

反応式

HRID 2419564 の反応式
[I-].[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N+](C)C3C=CC=CC=3)[S:9][C:5]=2[CH:4]=1.Cl.[NH2:21][CH2:22][CH2:23][C:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[NH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[Cl:2][C:3]1[CH:19]=[CH:18][C:6]2[S:7][C:8](=[N:21][CH2:22][CH2:23][C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[NH:26][CH:25]=3)[S:9][C:5]=2[CH:4]=1

参加物

6

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 67652Tryptamine hydrochlorideHCID 203138445-Chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide

生成物 1

HCID 20313872N-(5-Chloro-1,3-benzodithiol-2-ylidene)-1H-indole-3-ethanamine収率 12.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5-chloro-N-methyl-N-phenyl-1,3-benzodithiol-2-iminium iodide (8.39g), tryptamine hydrochloride (3.94g) and anhydrous sodium carbonate (2.12g) in 300 ml of anhydrous dimethylformamide is heated at 130° C under a nitrogen atmosphere for 3 hours. After this time the reaction mixture is poured into 1 liter of water and extracted with three 300 ml portions of benzene. The combined benzene extracts are dried over anhydrous sodium sulfate and then concentrated in vacuo to yield an oil. This oil is chromatographed on 600 ml of silica gel eluting first with dichloromethane/pentane (1:1) and finally dichloromethane. The resultant product with Rf =0.36 (silica gel-dichloromethane) is recrystallized from dichloromethane/pentane to yield 840 mg of the title compound, melting point 145°-147° C.

後処理

  1. extractionextracted with three 300 ml portions of benzene
  2. dry with materialThe combined benzene extracts are dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto yield an oil
  5. customThis oil is chromatographed on 600 ml of silica gel eluting first with dichloromethane/pentane (1:1) and finally dichloromethane
  6. customThe resultant product with Rf =0.36 (silica gel-dichloromethane) is recrystallized from dichloromethane/pentane

出典と根拠

ORDレコード
ord-9e7cda55bbdc47d08cbdeb767d76359d
出典データセット
uspto-grants-1978_08
特許番号
US04107175

反応ノート

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