Pyridine → N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 1715226

反応式

HRID 1715226 の反応式
[C:1]([C:4]1[S:8][C:7]([NH2:9])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:17](Cl)(=[O:19])[CH3:18]>C1COCC1.C(Cl)Cl>[C:1]([C:4]1[S:8][C:7]([NH:9][C:17](=[O:19])[CH3:18])=[N:6][C:5]=1[CH3:10])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 7208825-Acetyl-2-amino-4-methylthiazole

生成物 1

HCID 830648N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide収率 83.6%

試薬・触媒・溶媒 1

HCID 21919333Tetrahydrofurane dichloromethane溶媒

反応条件

温度
0 °C

実験手順

5-Acetyl-2-amino-4-methylthiazole (P5)(Flrochem)(12.4 g, 79 mmol) is suspended in THF/DCM 3:2 mixture (150 ml). The mixture is cooled down to 0° C. and pyridine (16 ml) is added, followed by the dropwise addition of acetyl chloride (8.43 ml, 119 mmol, 1.5 eq.). The mixture is stirred 2 hours at 0° C. As the acetylation is complete, the reaction is quenched with addition of water (70 ml) and diluted with EtOAc (100 ml). The two phases are separated and the organic phase is washed with one portion of 10% citric acid solution. Organic layer is dried over MgSO4, filtrated and evaporated. The resulting crude mass is purified by crystallization in EtOAc/Cyclohexane mixture, to obtain N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide (P6) as a colorless powder (13.1 g, 83.6% yield). 1H NMR (DMSO-d6) δ: 2.17 (s, 3H), 2.47 (s, 3H), 2.56 (s, 3H), 12.44 (br s, 1H). M− (ESI): 197.3; M+ (ESI): 199.3. HPLC (method A), Rt: 1.7 min (purity: 99.7%).

後処理

  1. customthe reaction is quenched with addition of water (70 ml)
  2. additiondiluted with EtOAc (100 ml)
  3. customThe two phases are separated
  4. washthe organic phase is washed with one portion of 10% citric acid solution
  5. dry with materialOrganic layer is dried over MgSO4
  6. filtrationfiltrated
  7. customevaporated
  8. customThe resulting crude mass is purified by crystallization in EtOAc/Cyclohexane mixture

出典と根拠

ORDレコード
ord-92845478cba64cf58275b52b05a14244
出典データセット
uspto-grants-2010_09
特許番号
US07799814B2

関連ノート

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