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

HRID 1676907

反応式

HRID 1676907 の反応式
[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]

参加物

4

反応物 3

HCID 887Methanol2 回HCID 2471BumetanideHCID 24386Thionyl Chloride

生成物 1

HCID 16657174Methyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate収率 89%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-116501f3cad34edbb04b7ab9a39decb9
出典データセット
uspto-grants-2011_08
特許番号
US08008283B2

関連ノート

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