3H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl- → 4-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289823노트

반응식

HRID 1289823 반응식
[CH3:1][N:2]1[C:6](=[O:7])[CH2:5][C:4]([CH3:8])=[N:3]1.[F-].[K+].Cl[CH2:12][N:13]1[C:17](=[O:18])[C:16]2[C:19]([CH:25]([CH3:27])[CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:15]=2[S:14]1(=[O:29])=[O:28]>CN(C=O)C>[CH:25]([C:19]1[C:16]2[C:17](=[O:18])[N:13]([CH2:12][O:7][C:6]3[N:2]([CH3:1])[N:3]=[C:4]([CH3:8])[CH:5]=3)[S:14](=[O:29])(=[O:28])[C:15]=2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=1)([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 176733H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl-HCID 522689Potassium FluorideHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxide

생성물 1

HCID 189225454-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide수율 37%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2,4-dihydro-2,5-dimethyl-3H-pyrazol-3-one (475 mg; 4.24 mmol) in DMF (25 ml) was added 280 mg (4.83 mmol) of KF followed by 2-chloromethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (1 g, 3.3 mmol), and the resulting mixture was stirred at room temperature for 24 hours and then was poured into ice/water. The above mixture was extracted with ethyl acetate and the organic layer was washed with water, dried, and concentrated in vacuo. The residue was purified by flash chromatography to afford 0.46 g (37%) of 4-isopropyl-6-methoxy-2-(1,3-dimethylpyrazol-5-yl-oxymethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =R2 =CH3 ; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. 146°-147° C.

후처리

  1. extractionThe above mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-0325d04e602d45639edf762f2127e922
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750550

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