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

HRID 1287771Notes

Reaction equation

HRID 1287771 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. Then 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. customThen excess of ammonia and acetone were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-832afd2fc2ed40a1a0d7674229c98458
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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