Ammonia → 3-Butylamino-4-phenoxy-5-sulphamyl-benzamide

HRID 918659Notes

Reaction equation

HRID 918659 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9](O)=[O:10])[CH2:2][CH2:3][CH3:4].C([N:28](CC)CC)C.CS(Cl)(=O)=O.N>CC(C)=O>[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]=1[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:9]([NH2:28])=[O:10])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 2471BumetanideHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 215060653-Butylamino-4-phenoxy-5-sulphamyl-benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 3-butylamino-4-phenoxy-5-sulphamyl-benzoic acid (1 g) in dry acetone (10 ml), triethylamine (0.278 g) was added. Methanesulphonyl chloride (0.315 g) in dry acetone (5 ml) was added to the reaction mixture, while stirring. The agitation was continued for 1.5 hours at 20°C. The resulting solution of the mixed anhydride was added dropwise to aqueous ammonia (30 ml containing 7 g of ammonia), while stirring. The excess of ammonia and acetone were removed by evaporation under reduced pressure. The pH of the reaction mixture was adjusted to 7.5 by means of 4N hydrochloric acid, and the precipitated 3-butylamino-4-phenoxy-5-sulphamyl-benzamide was isolated by filtration and recrystallized several times from aqueous ethanol. After drying in vacuo at 115°C, the compound was obtained with a melting point of 223°-224°C.

Workup

  1. stirringwhile stirring
  2. customThe excess of ammonia and acetone were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-54ad9219353c4848862cb3e70bd34339
Source dataset
uspto-grants-1976_07
Patent number
US03971819

Reaction notes

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