Tetrahydrofuran → 2-Chloro-4-methyl-5-(4-methylpyridin-2-ylcarbonyl)thiazole

HRID 1059886노트

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HRID 1059886 반응식
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([CH3:7])[N:6]=1.C([Li])CCC.[C:13]([C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=1)#N.[Cl-].[NH4+].[O:24]1CCCC1>CCCCCC>[Cl:1][C:2]1[S:3][C:4]([C:13]([C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=2)=[O:24])=[C:5]([CH3:7])[N:6]=1

참가 물질

7

반응물 5

HCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 887392-Cyano-4-methylpyridineHCID 30153282-Chloro-4-methylthiazoleHCID 178418339Butyllithium

생성물 1

HCID 186309862-Chloro-4-methyl-5-(4-methylpyridin-2-ylcarbonyl)thiazole

시약·촉매·용매 1

HCID 8058Hexane용매

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온도
-70 °C

실험 절차

To a stirred solution of 2-chloro-4-methylthiazole (6.35 g) in tetrahydrofuran (50 ml) was added a solution of n-butyllithium in n-hexane (1.66M, 34.35 ml) dropwise at −70° C. under a nitrogen atmosphere, and the mixture was stirred for 20 minutes at −70° C. To the resultant mixture was added a solution of 2-cyano-4-methylpyridine (3.74 g) in tetrahydrofuran (30 ml) dropwise at −70° C., and the mixture was stirred for 15 minutes. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (silica gel 240 g, n-hexane:ethyl acetate=10:1) to give 2-chloro-4-methyl-5-(4-methylpyridin-2-ylcarbonyl)thiazole (1.64 g).

후처리

  1. stirringthe mixture was stirred for 15 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel 240 g, n-hexane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-96d0b7188cd64fb7b4952e8bc00dc267
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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