1,2-Dichloroethane → 4-Chloro-N-(4-pentyl-bicyclo[2.2.2]octane-1-carbonyl)-benzenesulfonamide

HRID 1455546Notes

Reaction equation

HRID 1455546 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(Cl)CCl.[CH2:16]([C:21]12[CH2:28][CH2:27][C:24]([C:29](O)=[O:30])([CH2:25][CH2:26]1)[CH2:23][CH2:22]2)[CH2:17][CH2:18][CH2:19][CH3:20]>CN(C1C=CN=CC=1)C.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:29]([C:24]23[CH2:25][CH2:26][C:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])([CH2:28][CH2:27]2)[CH2:22][CH2:23]3)=[O:30])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 668244-ChlorobenzenesulfonamideHCID 42414664-Pentylbicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 684417734-Chloro-N-(4-pentyl-bicyclo[2.2.2]octane-1-carbonyl)-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

0.42 g of 4-chlorophenylsulfonamide, 60 mg of DMAP and 0.42 g of EDC are added to a solution of 0.5 g of 4-pentyl-bicyclo[2.2.2]octane-1-carboxylic acid in 8 ml of DMF, the mixture obtained is stirred for ca. 16 h at RT and solvent from the mixture obtained is evaporated. The evaporation residue obtained is dissolved in EtAc and washed with 1 N HCl, saturated NaHCO3 solution and brine and the organic phase obtained is dried. Solvent of the organic phase obtained is evaporated and the evaporation residue obtained is subjected to chromatography. 4-Chloro-N-(4-pentyl- bicyclo[2.2.2]octane-1-carbonyl)-benzenesulfonamide is obtained in the form of a white powder;

Workup

  1. customthe mixture obtained
  2. customsolvent from the mixture obtained
  3. customis evaporated
  4. customThe evaporation residue obtained
  5. dissolutionis dissolved in EtAc
  6. washwashed with 1 N HCl, saturated NaHCO3 solution and brine
  7. customthe organic phase obtained
  8. customis dried
  9. customSolvent of the organic phase obtained
  10. customis evaporated
  11. customthe evaporation residue obtained

Sources & evidence

ORD record
ord-356bd4791c184ed6818a06a875ebc721
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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