Ammonium Chloride → 5-Cyano-7-methylthioimidazo[5,1-b]thiazole

HRID 1839333노트

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HRID 1839333 반응식
C([Mg]Br)C.C1COCC1.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.C1(C)C=CC(S([C:30]#[N:31])(=O)=O)=CC=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[C:30]([C:11]1[N:18]2[C:14]([S:15][CH:16]=[CH:17]2)=[C:13]([S:19][CH3:20])[N:12]=1)#[N:31]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 87946p-Toluenesulphonyl cyanideHCID 23449208HCID 23449208, 화합물HCID 178420660HCID 178420660, 화합물

생성물 1

HCID 234492205-Cyano-7-methylthioimidazo[5,1-b]thiazole수율 49.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
-5 °C

실험 절차

A 1 M ethylmagnesium bromide/THF solution (2.0 ml) was added in an argon atmosphere at −40° C. to a solution of 405 mg of 5-iodo-7-methylthioimidazo[5,1-b]thiazole in 12 ml of dry THF. The mixture was stirred at the same temperature for 30 min. p-Toluenesulfonyl cyanide (372 mg) was added thereto. The temperature of the system was raised to −5° C. over a period of one hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture. Ethyl acetate was added thereto, followed by washing with saturated brine. 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=3:1:1) to give 131 mg of 5-cyano-7-methylthioimidazo[5,1-b]thiazole.

후처리

  1. additionwas added
  2. washby washing with saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:ethyl acetate:hexane=3:1:1)

출처 및 근거

ORD 기록
ord-6243bd4cea154a57b9bc7521be3e4332
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06677331B2

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