Potassium Carbonate → Methyl 10-(4-chlorobenzenesulphonamido)decanoate

HRID 358640Notes

Reaction equation

HRID 358640 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:14][O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:25][S:22]([C:19]1[CH:18]=[CH:17][C:16]([Cl:15])=[CH:21][CH:20]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 668244-ChlorobenzenesulfonamideHCID 554079Methyl 10-bromodecanoate

Product 1

HCID 20066951Methyl 10-(4-chlorobenzenesulphonamido)decanoateYield 39.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 10-bromodecanoate (1.5 g, 0.006 mol), 4-chlorobenzenesulphonamide (3.44 g, 0.018 mol), potassium carbonate (6.2 g, 0.045 mol) and dimethylformamide (50 ml) was heated at 100°-120° C. for 3 hours. After cooling, the inorganic material was removed by filtration. The filtrate was evaporated to dryness and the residue was extracted with dichloromethane. The residual oil obtained by evaporation was chromatographed on silica gel in petroleum ether (40°-60° C.) and the solid obtained on evaporation of the eluate was recrystallised (ether-pet. ether 40°-60°) to give the title compound (0.9 g, m.p. 68°-70° C.).

Workup

  1. temperaturewas heated at 100°-120° C. for 3 hours
  2. temperatureAfter cooling
  3. customthe inorganic material was removed by filtration
  4. customThe filtrate was evaporated to dryness
  5. extractionthe residue was extracted with dichloromethane
  6. customThe residual oil obtained by evaporation
  7. customwas chromatographed on silica gel in petroleum ether (40°-60° C.)
  8. customthe solid obtained on evaporation of the eluate
  9. customwas recrystallised (ether-pet. ether 40°-60°)

Sources & evidence

ORD record
ord-b8f3ea3f3bc04327ae86e2c913dffcaf
Source dataset
uspto-grants-1991_03
Patent number
US04997847

Reaction notes

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