Sodium Carbonate → HCID 21754064, compound

HRID 1728397Notes

Reaction equation

HRID 1728397 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([S:12]([OH:15])(=[O:14])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].[NH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][S:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH2:31][CH2:30]1>C(N(CC)CC)C.ClCCl.CN(C)C=O>[Cl:1][C:2]1[C:11]2[N:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]([S:12]([NH:26][CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][S:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[CH2:31][CH2:30]2)(=[O:14])=[O:15])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 190071168-Chloroquinoline-5-sulfonic acidHCID 19018054HCID 19018054, compound

Product 1

HCID 21754064HCID 21754064, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 14.2 g of 8-chloro-5-quinolinesulfonic acid were added 142 ml of thionyl chloride and 1.42 ml of dimethylformamide. The resultant mixture was heated under reflux for 3 hours and the thionyl chloride was removed by distillation under reduced pressure to obtain a residue. The thus obtained residue was dissolved in 100 ml of ice water and adjusted to a pH of 6 with a saturated aqueous sodium carbonate solution, followed by extraction with 100 ml of dichloromethane to obtain a dichloromethane phase. The dichloromethane phase was added dropwise to 100 ml of a dichloromethane solution containing 16.3 g of 1-(2-aminoethyl)-4-[3-(phenylthio)propyl]piperazine and 6.5 g of triethylamine over 30 minutes while cooling with ice. The resultant mixture was stirred at a temperature of 15° C. to 20° C. for 2 hours to carry out a reaction. After completion of the reaction, the resultant mixture was washed with 200 ml of water and dried over anhydrous magnesium sulfate. Then, solvent removal was conducted by distillation under reduced pressure to obtain a residue. The thus obtained residue was subjected to purification by means of a column for chromatography packed with 250 g of silica gel (Wakogel C-200, manufactured by Wako Pure Chemical Industries, Ltd., Japan), using a mixed solvent comprised of methanol and chloroform (2% methanol) as an eluent, to thereby obtain 21.2 g of 1-(8-chloro-5-quinolinesulfonylaminoethyl)-4-[3-(phenylthio)propyl]piperazine (1) (yield: 72%) .

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe thionyl chloride was removed by distillation under reduced pressure
  3. customto obtain a residue
  4. extractionfollowed by extraction with 100 ml of dichloromethane
  5. customto obtain a dichloromethane phase
  6. temperaturewhile cooling with ice
  7. customa reaction
  8. customAfter completion of the reaction
  9. washthe resultant mixture was washed with 200 ml of water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThen, solvent removal
  12. distillationwas conducted by distillation under reduced pressure
  13. customto obtain a residue
  14. customThe thus obtained residue was subjected to purification by means of a column for chromatography

Sources & evidence

ORD record
ord-dde5b1d755234632b8a6459b0ed1dcb4
Source dataset
uspto-grants-1994_07
Patent number
US05326870

Reaction notes

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