Bumetanide → N,N-diethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzamide

HRID 1676910Notes

Reaction equation

HRID 1676910 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:23]([OH:25])=O)[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.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:47]([NH:49][CH2:50][CH3:51])[CH3:48]>ClCCl>[CH2:47]([N:49]([CH2:50][CH3:51])[C:23](=[O:25])[C:8]1[CH:7]=[C:6]([NH:5][CH2:4][CH2:3][CH2:2][CH3:1])[C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:10]([S:19]([NH2:22])(=[O:21])=[O:20])[CH:9]=1)[CH3:48]

Participants

6

Reactant 4

HCID 2471BumetanideHCID 8021DiethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-Hydroxybenzotriazole

Product 1

HCID 11509988N,N-diethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzamideYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bumetanide (1.16 g, 3.2 mmol) was dissolved in dichloromethane (10 mL) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, 690 mg, 3.6 mmol) was added. After 5 minutes N-hydroxybenzotriazole (HOBt, 498 mg, 3.6 mmol) was added and the solution was stirred for an additional 5 minutes. Diethylamine (332 uL, 3.2 mmol) was added and the reaction was stirred for 2 hours. The reaction was washed with saturated sodium bicarbonate, water and brine, and dried with magnesium sulfate. The dichloromethane was removed under reduced pressure to yield 860 mg (65%) of pure N,N-diethyl 3-aminosulfonyl-5-butylamino-4-phenoxybenzamide.

Workup

  1. stirringthe reaction was stirred for 2 hours
  2. washThe reaction was washed with saturated sodium bicarbonate, water and brine
  3. dry with materialdried with magnesium sulfate
  4. customThe dichloromethane was removed under reduced pressure

Sources & evidence

ORD record
ord-63e1b78e3ae14614a1ca14d84a22548f
Source dataset
uspto-grants-2011_08
Patent number
US08008283B2

Reaction notes

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