Bumetanide → HCID 16657175, compound

HRID 1287769Notes

Reaction equation

HRID 1287769 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]([OH:11])=[O:10])[CH2:2][CH2:3][CH3:4].Cl[CH2:27][C:28]#[N:29].C(N(CC)CC)C>CC(C)=O>[C:28]([CH2:27][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([S:22](=[O:25])(=[O:24])[NH2:23])[C:14]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH:7]=1)#[N:29]

Participants

5

Reactant 3

HCID 2471BumetanideHCID 7856ChloroacetonitrileHCID 8471Triethylamine

Product 1

HCID 16657175HCID 16657175, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3-n-butylamino-4-phenoxy-5-sulphamyl-benzoic acid (1 g), chloroacetonitrile (0.625 g), triethylamine (0.28 g), and dry acetone (10 ml) was refluxed for 19 hours. After cooling, the precipitated triethylamine hydrochloride was removed by filtration, and the filtrate was evaporated in vacuo. To the residue, water (20 ml) and ethylacetate (50 ml) were added, and the pH of the aqueous layer was adjusted to pH 7.5. The organic layer was then separated, washed with dilute sosium hydrogen carbonate, dried, and evaporated in vacuo. The residue was recrystallized several times from chloroform/petroleum ether. Thereby the cyanomethyl-3-n-butylamino-4-phenoxy-5-sulphamyl-benzoate was obtained with a melting point of 159°-161° C.

Workup

  1. temperaturewas refluxed for 19 hours
  2. temperatureAfter cooling
  3. customthe precipitated triethylamine hydrochloride was removed by filtration
  4. customthe filtrate was evaporated in vacuo
  5. additionTo the residue, water (20 ml) and ethylacetate (50 ml) were added
  6. customThe organic layer was then separated
  7. washwashed
  8. additionwith dilute sosium hydrogen carbonate
  9. customdried
  10. customevaporated in vacuo
  11. customThe residue was recrystallized several times from chloroform/petroleum ether

Sources & evidence

ORD record
ord-c19217006b8143f2988d1b47be62e285
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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