Dimethylformamide → 4-Chloro-2-ethyl-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide

HRID 729253ノート

反応式

HRID 729253 の反応式
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[CH2:7]([N:9]1C(=O)C(O)=[C:11]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[S:10]1(=[O:27])=[O:26])[CH3:8].CN(C=O)C>C(Cl)Cl>[Cl:6][C:1]1[C:2](=[O:3])[N:9]([CH2:7][CH3:8])[S:10](=[O:27])(=[O:26])[C:11]=1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68661688HCID 68661688、化合物

生成物 1

HCID 686618714-Chloro-2-ethyl-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide収率 71%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Oxalyl chloride (0.379 g, 2.99 mmol) was added dropwise to a solution of 2-ethyl-4-hydroxy-5-[4-(trifluoromethyl)phenyl]isothiazol-3(2H)-one 1,1-dioxide (0.480 g, 1.49 mmol) and DMF (0.109 g, 1.49 mmol) in DCM (12 mL). The mixture was refluxed for 1 h. It was evaporated and water was added. The resulting mixture was extracted with EtOAc, and the combined organic layers were washed with brine and evaporated to give the title compound (0.306 g, 71%) as a solid; 1H NMR (500 MHz, DMSO-d6): δ 8.07-8.11 (m, 4H), 3.81 (q, 2H), 1.33 (t, 3H).

後処理

  1. temperatureThe mixture was refluxed for 1 h
  2. customIt was evaporated
  3. additionwater was added
  4. extractionThe resulting mixture was extracted with EtOAc
  5. washthe combined organic layers were washed with brine
  6. customevaporated

出典と根拠

ORDレコード
ord-97cca3e7a7af49b5a7379c80f8dbe2a3
出典データセット
uspto-grants-2009_09
特許番号
US07582629B2

反応ノート

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