Water → N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-benzoxathiole-4-sulfonamide

HRID 542687노트

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HRID 542687 반응식
[O:1]1[C:5]2=[CH:6][CH:7]=[CH:8][C:9]([S:10]([NH2:13])(=[O:12])=[O:11])=[C:4]2[S:3][CH2:2]1.C[Al](C)C.C[O:19][C:20](=O)[NH:21][C:22]1[N:27]=[C:26]([O:28][CH3:29])[CH:25]=[C:24]([CH3:30])[N:23]=1.O>C(Cl)Cl.Cl.C(O)(=O)C>[CH3:29][O:28][C:26]1[CH:25]=[C:24]([CH3:30])[N:23]=[C:22]([NH:21][C:20]([NH:13][S:10]([C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[O:1][CH2:2][S:3][C:4]=23)(=[O:12])=[O:11])=[O:19])[N:27]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 13072161Methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamateHCID 16682925TrimethylaluminumHCID 201377521,3-Benzoxathiole-4-sulfonamide

생성물 1

HCID 20137750N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-benzoxathiole-4-sulfonamide

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 2.2 g 1,3-benzoxathiole-4-sulfonamide, prepared in Example 13, in 50 ml methylene chloride at ambient temperature under nitrogen is added 5.5 ml trimethylaluminum (2M in toluene). After stirring 15 minutes at ambient temperature, 2.0 g of methyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according to the procedure of Example 3, is added and the reaction mixture is heated at reflux for 16 hours. The reaction mixture is cooled to ambient temperature and 75 ml water, 10 ml glacial acetic acid, and 10 drops hydrochloric acid are sequentially added. The organic phase is separated, dried, and the solvent removed under reduced pressure to give an oil. Crystallization of the oil from n-butyl chloride/ether gives a solid.

후처리

  1. additionis added
  2. temperaturethe reaction mixture is heated
  3. temperatureat reflux for 16 hours
  4. temperatureThe reaction mixture is cooled to ambient temperature
  5. customThe organic phase is separated
  6. customdried
  7. customthe solvent removed under reduced pressure
  8. customto give an oil
  9. customCrystallization of the oil from n-butyl chloride/ether
  10. customgives a solid

출처 및 근거

ORD 기록
ord-7d8a0328dcaf4f68ab7a4f8329aa339e
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659368

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