S,S-dimethylmethanesulfinyl iodide → ethyl 9-bromo-5H-spiro[benzo[2,3]oxepino[4,5-d]thiazole-4,2'-oxirane]-2-carboxylate

HRID 575293ノート

反応式

HRID 575293 の反応式
CS(I)(C)(C)=O.[CH3:7][C:8]([O-:11])([CH3:10])[CH3:9].[K+].[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18]CC(=O)C3[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=3[C:16]=2[CH:15]=1>ClCCl>[Br:13][C:14]1[CH:33]=[CH:32][C:17]2[O:18][CH2:7][C:8]3([C:10]4[S:25][C:24]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:23][C:22]=4[C:16]=2[CH:15]=1)[CH2:9][O:11]3

参加物

5

反応物 3

HCID 2723795S,S-dimethylmethanesulfinyl iodideHCID 23665647Potassium tert-butoxideHCID 86693324Ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate

生成物 1

HCID 86693323ethyl 9-bromo-5H-spiro[benzo[2,3]oxepino[4,5-d]thiazole-4,2'-oxirane]-2-carboxylate収率 48%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of S,S-dimethylmethanesulfinyl iodide (1.15 g, 5.23 mmol, 1.60 equiv), t-BuOK (4 mL, 1.20 equiv) in dichloromethane (5 mL) at room temperature After 30 minutes a solution of ethyl 9-bromo-4-oxo-4,5-dihydrobenzo[2,3]oxepino[4,5-d]thiazole-2-carboxylate (1.2 g, 3.26 mmol, 1.00 equiv) in dichloromethane (10 mL) was added slowly. The resulting solution was stirred for 5 h at room temperature, quenched with water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19) to give 600 mg (48%) of the titled compound as a off-white solid; LC-MS 382,384[M+H]+.

後処理

  1. customInto a 100-mL 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customat room temperature
  4. customAfter 30 minutes
  5. additionwas added slowly
  6. customquenched with water
  7. extractionextracted with dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by a silica gel column with ethyl acetate/petroleum ether (1:19)

出典と根拠

ORDレコード
ord-026c435b8af84c57b5123d4c49c51426
出典データセット
uspto-grants-2015_05
特許番号
US09034866B2

反応ノート

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