Bumetanide → 3-Butylamino-4-(4-chlorosulphonylphenoxy)-5-sulphamyl-benzoic acid

HRID 918658Notes

Reaction equation

HRID 918658 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH2:6]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH3:9]>>[CH2:6]([NH:10][C:11]1[CH:12]=[C:13]([CH:17]=[C:18]([S:27](=[O:30])(=[O:29])[NH2:28])[C:19]=1[O:20][C:21]1[CH:22]=[CH:23][C:24]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:25][CH:26]=1)[C:14]([OH:16])=[O:15])[CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 2471BumetanideHCID 24638Chlorosulfonic acid

Product 1

HCID 215060243-Butylamino-4-(4-chlorosulphonylphenoxy)-5-sulphamyl-benzoic acid

Procedure

To chlorosulphonic acid (5 ml), 3-butylamino-4-phenoxy-5-sulphamyl-benzoic acid (1 g) was added in portions, while stirring and keeping the temperature below 45°C. The reaction mixture was stirred to 10 minutes and then poured into ice water (10 g of ice and 20 ml of water). The precipitated 3-butylamino-4-(4-chlorosulphonylphenoxy)-5-sulphamyl-benzoic acid was isolated by filtration and without further purification added to aqueous ammonia (10 ml containing 2.5 g of ammonia). Excess of ammonia was removed by evaporation, and the resulting solution was adjusted to pH 2.5 by addition of 4N hydrochloric acid. The precipitated 3-butylamino-4-(4-sulphamylphenoxy)-5-sulphamyl-benzoic acid was isolated by filtration, recrystallized from aqueous ethanol, and dried. The obtained compound had a melting point of 265°C.

Workup

  1. customthe temperature below 45°C
  2. stirringThe reaction mixture was stirred to 10 minutes

Sources & evidence

ORD record
ord-c5a9cfdf954d4a4896d0694802a6da89
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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