Sodium Carbonate → HCID 21754064, 화합물

HRID 1728397노트

반응식

HRID 1728397 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

HCID 21754064HCID 21754064, 화합물수율 72%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회HCID 8471Triethylamine용매

실험 절차

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%) .

후처리

  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

출처 및 근거

ORD 기록
ord-dde5b1d755234632b8a6459b0ed1dcb4
출처 데이터셋
uspto-grants-1994_07
특허 번호
US05326870

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