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

HRID 2405116

反応式

HRID 2405116 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 83.8%

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) (12.35 g, 79 mmol) is suspended in THF/DCM 3:2 mixture (150 mL). The mixture was 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 was 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 (13.13 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, 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-b3d7f982727d4bcf9a562f7aa7193a2b
出典データセット
uspto-grants-2014_08
特許番号
US08802861B2

関連ノート

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