N-Iodosuccinimide → 2-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole

HRID 1043656ノート

反応式

HRID 1043656 の反応式
[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[CH:14][N:9]3[N:8]=2)=[CH:4][CH:3]=1.[I:17]N1C(=O)CCC1=O>CN(C)C=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[S:11][C:10]3=[N:12][CH:13]=[C:14]([I:17])[N:9]3[N:8]=2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 673361162-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 673357762-(4-Fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole収率 71%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-(4-Fluoro-phenoxy)-imidazo[2,1-b][1,3,4]thiadiazole (0.6 g, 2.55 mmol) was dissolved in N,N-dimethylformamide (10 mL) and N-iodosuccinimide (0.63 g, 2.81 mmol) was added in one portion. The reaction mixture was stirred at room temperature overnight in the absence of light. The yellow suspension was filtered and rinsed with diethylether (2×2 mL) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.65 g, 71%). The filtrate was evaporated and the residue was triturated with diethylether (6 mL) and filtered. This solid was purified by column chromatography (Biotage™/Flash, silica, methanol:dichloromethane 0:10 to 1:9) to give 2-(4-fluoro-phenoxy)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole as a white solid (0.15 g, 16% yield).

後処理

  1. filtrationThe yellow suspension was filtered
  2. washrinsed with diethylether (2×2 mL)

出典と根拠

ORDレコード
ord-cdcd5fb59e744bbaadba6bad0d80bda9
出典データセット
uspto-grants-2013_10
特許番号
US08563550B2

反応ノート

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