Mesitylene → 5-(4-Phenylsulfonyl-butoxy)-carbostyril

HRID 1065378Notes

Reaction equation

HRID 1065378 reaction equation
[C:1]1([S:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH2:17][CH2:18][C:19](=[O:25])[NH:20]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=C(C)C=C(C)C=1>[Pd]>[C:1]1([S:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][C:19](=[O:25])[NH:20]3)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7947MesityleneHCID 205400365-(4-Phenylsulfonyl-butoxy)-3,4-dihydro-carbostyril

Product 1

HCID 205400375-(4-Phenylsulfonyl-butoxy)-carbostyril

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

100 mgm of 5-(4-phenylsulfonyl-butoxy)-3,4-dihydro-carbostyril were refluxed with 30 mgm of palladium-on-charcoal and 1 ml of mesitylene. After 3.5 hours, another 30 mgm of palladium-on-charcoal were added, and the mixture was heated for 9 hours more. Subsequently, the reaction mixture was filtered while still hot, the filtrate was evaporated, and the residue was chromatographed on a silica gel column with a mixture of benzene/ethanol/conc. ammonia=75/25/3. Besides unreacted starting material, 9 mgm of 5-(4-phenylsulfonyl-butoxy)-carbostyril were obtained.

Workup

  1. temperaturethe mixture was heated for 9 hours more
  2. filtrationSubsequently, the reaction mixture was filtered while still hot, the filtrate
  3. customwas evaporated
  4. customthe residue was chromatographed on a silica gel column with a mixture of benzene/ethanol/conc
  5. customwere obtained

Sources & evidence

ORD record
ord-3bca677e20e24d46b57db40e05049781
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

Loading…