Sodium Iodide → 2-Amino-3-benzoyl-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine

HRID 430622ノート

反応式

HRID 430622 の反応式
[NH2:1][C:2]1[S:10][C:5]2[CH2:6][NH:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CI.[C:21](=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[NH2:1][C:2]1[S:10][C:5]2[CH2:6][N:7]([CH3:21])[CH2:8][CH2:9][C:4]=2[C:3]=1[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15434454(2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-3-yl)phenylmethanone

生成物 1

HCID 154344492-Amino-3-benzoyl-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine収率 77%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

2-Amino-3-benzoyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine (2 mmol), as prepared in Example 8, and methyl iodide (3 mmol) were dissolved in dry dimethyformamide (20 mL). Finely ground anhydrous potassium carbonate (1.9 g) and sodium iodide (0.2 g) were added to the solution and the resulting mixture was warmed to 65° C. overnight under nitrogen. After this period (TLC control), the reaction mixture was cooled, diluted with water, extracted with diethyl ether (3×50 mL), and dried on sodium sulfate. The crude product was isolated and then purified by column chromatography eluting with ethyl acetate and petroleum ether solutions to give the desired compound. (m.p. 164-165° C.; 77% yield).

後処理

  1. waitAfter this period (TLC control)
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with diethyl ether (3×50 mL)
  4. customdried on sodium sulfate
  5. customThe crude product was isolated
  6. custompurified by column chromatography
  7. washeluting with ethyl acetate and petroleum ether solutions

出典と根拠

ORDレコード
ord-0e2708f340294bf081c6ad26630130f8
出典データセット
uspto-grants-2001_11
特許番号
US06323214B1

反応ノート

読み込み中…