Bumetanide → HCID 11519146, compound

HRID 1676912Notes

Reaction equation

HRID 1676912 reaction equation
[OH-].[CH2:2]([N+:9]([CH3:12])([CH3:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[CH:19]=[C:20]([C:35]([OH:37])=[O:36])[CH:21]=[C:22]([S:31]([NH2:34])(=[O:33])=[O:32])[C:23]=1[O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1.CCCCCCC>O>[NH2:34][S:31]([C:22]1[CH:21]=[C:20]([CH:19]=[C:18]([NH:17][CH2:16][CH2:15][CH2:14][CH3:13])[C:23]=1[O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:35]([O-:37])=[O:36])(=[O:32])=[O:33].[CH2:2]([N+:9]([CH3:12])([CH3:11])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 2471BumetanideHCID 8900HeptaneHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 11519146HCID 11519146, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of benzyltrimethylammonium hydroxide (451 mg, 2.7 mmol) in water (1 mL) was added bumetanide (1 g, 2.7 mmol) over a period of 5 minutes. The reaction mixture became clear after 10 minutes of stirring. The water was removed under reduced pressure to yield a crude colorless oil. Pure product was obtained from recrystallization of the oil with water and heptane to yield 690 mg of benzyltrimethylammonium 3-aminosulfonyl-5-butylamino-4-phenoxybenzoate as light pink crystals.

Workup

  1. customThe water was removed under reduced pressure
  2. customto yield a crude colorless oil

Sources & evidence

ORD record
ord-7ad5ced15249435d83295053e3e27d5c
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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