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

HRID 2421934
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HRID 2421934 반응식
[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]
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참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 67243180HCID 67243180, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
50 °C

실험 절차

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 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.

후처리

  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

출처 및 근거

ORD 기록
ord-f6a618cecabc489bb356cb5cbb3c8cdd
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960380B2

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