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

HRID 989868ノート

反応式

HRID 989868 の反応式
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]

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 87946p-Toluenesulphonyl cyanideHCID 23449208HCID 23449208、化合物HCID 178420660HCID 178420660、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2e3ad34fde524f83863269ae092ce735
出典データセット
uspto-grants-2002_10
特許番号
US06458780B1

反応ノート

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