Sodium Carbonate → HCID 21754064、化合物

HRID 1728397ノート

反応式

HRID 1728397 の反応式
[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

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 190071168-Chloroquinoline-5-sulfonic acidHCID 19018054HCID 19018054、化合物

生成物 1

HCID 21754064HCID 21754064、化合物収率 72%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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%) .

後処理

  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

出典と根拠

ORDレコード
ord-dde5b1d755234632b8a6459b0ed1dcb4
出典データセット
uspto-grants-1994_07
特許番号
US05326870

反応ノート

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