Methanol → Methyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate

HRID 1676907

반응식

HRID 1676907 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:23]([OH:25])=[O:24])[CH:9]=[C:10]([S:19]([NH2:22])(=[O:21])=[O:20])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1.S(Cl)(Cl)=O.[CH3:30]O>>[NH2:22][S:19]([C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:11]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:23]([O:25][CH3:30])=[O:24])(=[O:21])=[O:20]

참가 물질

4

반응물 3

HCID 887Methanol2회HCID 2471BumetanideHCID 24386Thionyl Chloride

생성물 1

HCID 16657174Methyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate수율 89%

실험 절차

To a slurry of bumetanide (1.2 g, 3.29 mmol) in methanol (12 mL) under nitrogen, was added a mixture of thionyl chloride (70 uL) in methanol (6 mL) over 5 minutes. After stirring for 5 minutes the reaction mixture became soluble. The reaction was stirred for an additional 30 minutes, at which time the reaction was complete as determined by thin layer chromatography (TLC). The methanol was removed under reduced pressure and the residue was brought up in ethyl acetate and washed with saturated sodium bicarbonate, water and brine. The ethyl acetate was dried over anhydrous magnesium sulfate and concentrated to yield 1.1 g (89%) of methyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate as a white solid.

후처리

  1. stirringThe reaction was stirred for an additional 30 minutes, at which time the reaction
  2. customThe methanol was removed under reduced pressure
  3. washwashed with saturated sodium bicarbonate, water and brine
  4. dry with materialThe ethyl acetate was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-116501f3cad34edbb04b7ab9a39decb9
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08008283B2

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