Potassium Carbonate → 4-(8-Oxo-7-propanoyl-decoxy)benzenesulfonamide

HRID 1389829Notes

Reaction equation

HRID 1389829 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([C:24](=[O:27])[CH2:25][CH3:26])[C:20](=[O:23])[CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[NH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([C:20](=[O:23])[CH2:21][CH3:22])[C:24](=[O:27])[CH2:25][CH3:26])=[CH:3][CH:4]=1)(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74093p-HydroxybenzenesulfonamideHCID 123634064-(6-Bromohexyl)heptane-3,5-dione

Product 1

HCID 5140774-(8-Oxo-7-propanoyl-decoxy)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 18.2 g, of 4-hydroxybenzenesulfonamide, 33.6 g of 4-(6-bromohexyl)-3,5-heptanedione, 18.3 g. of powdered anhydrous potassium carbonate and 175 ml. of acetone was stirred at reflux for 24 hours. The reaction mixture was cooled, filtered to remove salts, and concentrated in vacuo. The solid residue was recyrstallized from an acetone-ether mixture to give 4-[6-(4-aminosulfonylphenoxy)hexyl]-3,5-heptanedione, m.p. 86°-87° C. (light yellow solid).

Workup

  1. additionA mixture of 18.2 g
  2. temperatureat reflux for 24 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. customto remove salts
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f8a01e3fafa48b7bf9c62da754e4b58
Source dataset
uspto-grants-1981_01
Patent number
US04246284

Reaction notes

Loading…