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Dimethylformamide → 2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 729244
ノート
印刷プレビュー

反応式

HRID 729244 の反応式
[C:1]([Cl:6])(=O)[C:2](Cl)=[O:3].[C:7]([N:11]1C(=O)C(O)=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:12]1(=[O:25])=[O:24])([CH3:10])([CH3:9])[CH3:8].CN(C=O)C>C(Cl)Cl>[C:7]([N:11]1[C:2](=[O:3])[C:1]([Cl:6])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[S:12]1(=[O:25])=[O:24])([CH3:10])([CH3:8])[CH3:9]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67243180HCID 67243180、化合物

生成物 1

HCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide収率 480.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
50 °C

実験手順

Oxalyl chloride (3.39 g, 2.71 mmol) was added dropwise to a solution of 2-tert-butyl-4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide (5 g, 17.77 mol) and DMF (15 mL) in DCM (220 mL) at 0° C. The reaction mixture was then heated at 50° C. for 4 h, concentrated and the residue was diluted with EtOAc and washed with water, then brine and evaporated. The residue was purified by silica gel column chromatography, using a 98:2 mixture of petroleum ether and EtOAc as eluant. The product containing fractions were evaporated, the residue was triturated in petroleum ether and the solvent was decanted to give the title compound (3.9 g, 74%) as a solid; 1H NMR (500 MHz, CDCl3): δ 7.97-7.92 (m, 2H), 7.61-7.51 (m, 3H), 1.75 (s, 9H); 13C NMR (125 MHz, CDCl3): δ 156.5, 142.8, 132.3, 129.3, 128.8, 123.4, 63.0, 27.7.

後処理

  1. concentrationconcentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with water
  4. custombrine and evaporated
  5. customThe residue was purified by silica gel column chromatography
  6. additiona 98:2 mixture of petroleum ether and EtOAc as eluant
  7. additionThe product containing fractions
  8. customwere evaporated
  9. customthe residue was triturated in petroleum ether
  10. customthe solvent was decanted

出典と根拠

ORDレコード
ord-1c1ee577221b48078b32b5a6681da06c
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07582629B2

反応ノート

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