Acetic Acid → 3-[3-(6-Methoxy-3,4-xylyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 1274545노트

반응식

HRID 1274545 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[C:15]([O:16][CH3:17])=[CH:14][C:13]([CH3:18])=[C:12]([CH3:19])[CH:11]=3)[C:6]=2[CH:20]=1.CN(C)[C:23]1[O:24][C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=1.C(O)(=O)C.O>C(Cl)Cl.C(OCC)C>[CH3:17][O:16][C:15]1[C:10]([C:7]2[C:6]3[CH:20]=[C:2]([N:1]4[C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[NH:28][C:23]4=[O:24])[CH:3]=[CH:4][C:5]=3[S:9][N:8]=2)=[CH:11][C:12]([CH3:19])=[C:13]([CH3:18])[CH:14]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 183145035-Amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole

생성물 1

HCID 154776123-[3-(6-Methoxy-3,4-xylyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione수율 62.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A mixture of 5-amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole (8.53 g, 30.0 mmol), 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (6.87 g, 33.0 mmol) and acetic acid is refluxed for 2 hours, cooled, and poured into water. The resultant aqueous mixture is filtered to obtain a solid. A solution of the solid in methylene chloride is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 5% diethyl ether in methylene chloride solution gives the title product as a yellow foam (8.37 g, 62.0%) which is identified by NMR spectral analyses.

후처리

  1. temperatureis refluxed for 2 hours
  2. temperaturecooled
  3. filtrationThe resultant aqueous mixture is filtered
  4. customto obtain a solid
  5. washA solution of the solid in methylene chloride is washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain an oil

출처 및 근거

ORD 기록
ord-9d1e892e80704d99a6cb91d363b8005e
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156700

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