Acetyl chloride → 5-Acetyl-7-methylthioimidazo[5,1-b]thiazole

HRID 1839332노트

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HRID 1839332 반응식
C([Mg]Br)C.C1C[O:8][CH2:7][CH2:6]1.I[C:11]1[N:18]2[C:14]([S:15][CH:16]=[CH:17]2)=[C:13]([S:19][CH3:20])[N:12]=1.C(Cl)(=O)C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:7]([C:11]1[N:18]2[C:14]([S:15][CH:16]=[CH:17]2)=[C:13]([S:19][CH3:20])[N:12]=1)(=[O:8])[CH3:6]

참가 물질

7

반응물 4

HCID 6367Acetyl chlorideHCID 25517Ammonium ChlorideHCID 23449208HCID 23449208, 화합물HCID 178420660HCID 178420660, 화합물

생성물 1

HCID 234491715-Acetyl-7-methylthioimidazo[5,1-b]thiazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-5 °C

실험 절차

A 1 M ethylmagnesium bromide/THF solution (4.78 ml) was added in an argon atmosphere at −40° C. to a solution of 963 mg of 5-iodo-7-methylthioimidazo[5,1-b]thiazole in 30 ml of dry THF. The mixture was stirred at the same temperature for 30 min. Acetyl chloride (0.35 ml) was added thereto. The temperature of the system was raised to −5° C. over a period of 2 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Ethyl acetate was added thereto, followed by washing with a dilute aqueous sodium thiosulfate solution and saturated brine in that order. The organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by distillation. The residue was purified by column chromatography on silica gel (dichloromethane:ethyl acetate:hexane=2:1:1) to give 384 mg of 5-acetyl-7-methylthioimidazo[5,1-b]thiazole.

후처리

  1. washby washing with a dilute aqueous sodium thiosulfate solution and saturated brine in that order
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was removed by distillation
  4. customThe residue was purified by column chromatography on silica gel (dichloromethane:ethyl acetate:hexane=2:1:1)

출처 및 근거

ORD 기록
ord-d411427771104247aeae62642b245c5e
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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