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

HRID 1676907

Reaction equation

HRID 1676907 reaction equation
[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]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 2471BumetanideHCID 24386Thionyl Chloride

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-116501f3cad34edbb04b7ab9a39decb9
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Linked notes

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