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

HRID 2405116

반응식

HRID 2405116 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 830648N-(5-acetyl-4-methyl-1,3-thiazol-2-yl)acetamide수율 83.8%

시약·촉매·용매 1

HCID 21919333Tetrahydrofurane dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b3d7f982727d4bcf9a562f7aa7193a2b
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802861B2

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