Triethylamine → 2-(5-(Methylthio)thiazol-2-ylcarbamoyl)phenyl acetate

HRID 1620890

反応式

HRID 1620890 の反応式
[C:1]([O:4][C:5]1[C:6](=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH3:14][S:15][C:16]1[S:20][C:19]([NH2:21])=[N:18][CH:17]=1.C(N(CC)CC)C>C1COCC1>[C:1]([O:4][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](=[O:8])[NH:21][C:19]1[S:20][C:16]([S:15][CH3:14])=[CH:17][N:18]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chlorideHCID 3516785-(Methylthio)thiazol-2-amine

生成物 1

HCID 497757802-(5-(Methylthio)thiazol-2-ylcarbamoyl)phenyl acetate収率 98.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under nitrogen a solution of acetylsalicyloyl chloride (1.24 g, 6.20 mmol, 1.3 eq) in THF (40 mL) was added to a stirred solution of 5-(methylthio)thiazol-2-amine 514 (700.0 mg, 4.79 mmol, 1.0 eq) in dry THF (5 mL). This was followed by the addition of triethylamine (0.67 mL, 4.79 mmol, 1.0 eq). The reaction mixture was stirred at room temperature and monitored by TLC. After two hours, reaction was filtered through sintered funnel and solvent removed in vacuo. The crude product was dissolved in EtOAc (150 mL) and washed twice each with 1M HCl and saturated aq. sodium hydrogen carbonate solutions. The organic fraction was dried over MgSO4 followed the removal of solvent. Flash column chromatography yielded the pure product 518 (1.450 g, 98%) as a solid.

後処理

  1. customreaction
  2. filtrationwas filtered through sintered funnel
  3. customsolvent removed in vacuo
  4. dissolutionThe crude product was dissolved in EtOAc (150 mL)
  5. washwashed twice each with 1M HCl and saturated aq. sodium hydrogen carbonate solutions
  6. dry with materialThe organic fraction was dried over MgSO4
  7. customthe removal of solvent

出典と根拠

ORDレコード
ord-bc8ead42c3864851abac941a06c4ae38
出典データセット
uspto-grants-2014_07
特許番号
US08772502B2

関連ノート

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