Dimethylformamide → HCID 22966909、化合物

HRID 2306000ノート

反応式

HRID 2306000 の反応式
[N:1]([CH2:4][CH2:5][CH3:6])=[C:2]=[S:3].CN(C)C=O.[NH2:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>O>[CH2:4]([NH:1][C:2](=[S:3])[NH:12][C:13]1[S:14][CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:5][CH3:6]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 69403Propyl IsothiocyanateHCID 78381Methyl 2-amino-3-thenoate

生成物 1

HCID 22966909HCID 22966909、化合物収率 40.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
132.5 °C

実験手順

In a sulfonation flask, 2.02 g (0.02 mol) of 1-isothiocynatopropane are added dropwise to 30 ml dimethylformamide and 3.0 g (0.019 mol) of methyl 2-aminothiophene-3-carboxylate. The reaction mixture is then stirred at 130-135° C. for 12 hours and after cooling added to 120 ml of water. The resulting mixture is then extracted three times with ethylacetate and the separated organic phase dried over sodium sulfate. The solvent is then removed in a water-jet vacuum, giving the crude product as a dark oil, which is purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3). 2.0 g of methyl 2-(3-propylthioureido)thiophene-3-carboxylate are obtained in the form of a yellow powder having a melting point of 122-124° C.

後処理

  1. temperatureafter cooling
  2. extractionThe resulting mixture is then extracted three times with ethylacetate
  3. dry with materialthe separated organic phase dried over sodium sulfate
  4. customThe solvent is then removed in a water-jet vacuum
  5. customgiving the crude product as a dark oil, which
  6. customis purified by column chromatography over silica gel (eluant: tert.butylmethylether/hexane=2:3)

出典と根拠

ORDレコード
ord-301c832c24364a8789e8b94b397fcabb
出典データセット
uspto-grants-2002_08
特許番号
US06441169B1

反応ノート

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