Dimethylformamide → HCID 69585794、化合物

HRID 889896ノート

反応式

HRID 889896 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[S:10][C:3]=12.CN(C=O)C.Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[CH2:24]([O:23][C:21]([C:20]1[S:13][C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[N:12][C:26]=1[CH3:28])=[O:22])[CH3:25]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 11858Ethyl 2-chloroacetoacetateHCID 235951097-Chlorothieno[3,2-b]pyridine-2-carbothioamide

生成物 1

HCID 69585794HCID 69585794、化合物収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

19.5 g (85.6 mmol) of 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide was added to 160 mL of a 1:1 DMF:THF solution mixture and cooled to 0° C. To this solution was slowly added 17.7 mL (128 mmol) of ethyl 2-chloroacetoacetate. After addition, the reaction was heated to 80° C. for sixteen hours. The reaction was cooled to room temperature and extracted with dichloromethane and water. The organic layer was separated and dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to afford 2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (15.6 g) in 54% yield. C14H11ClN2O2S2: APCI m/z 339.1/341.0 (pos.); 1H NMR (CDCl3): δ 8.68 (d, 1H , J=5.4 Hz), 8.24 (s, 1H), 7.51 (d, 1H, J=5.4 Hz), 4.36 (q, 2H, J=7.1 Hz), 2.77 (s, 3H), 1.38 (t, 3H, J=7.1 Hz) ppm.

後処理

  1. additionAfter addition
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-ae94746106f24abbab2665600e567b57
出典データセット
uspto-grants-2006_02
特許番号
US06995171B2

反応ノート

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