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Dimethylformamide → N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide

HRID 1903197
ノート
印刷プレビュー

反応式

HRID 1903197 の反応式
CN(C)C=O.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.C([O-])([O-])=O.[K+].[K+].[OH:24][CH2:25][CH2:26][N:27]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[C:28](=[O:33])[CH2:29][CH2:30][CH2:31]Cl>C(Cl)(Cl)Cl>[OH:24][CH2:25][CH2:26][N:27]([CH:34]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]1)[C:28]([CH2:29][CH2:30][CH2:31][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)=[O:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 12836954N-(2-hydroxyethyl)-N-(4-chlorobutyryl)cyclohexylamine

生成物 1

HCID 12866343N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide収率 12.5%

試薬・触媒・溶媒 1

HCID 6212
Chloroform
溶媒

実験手順

Into 50 ml of dimethylformamide were added 1.73 g of 6-hydroxycarbostyril, 1.8 g of K2CO3 and 0.5 g of KI. The mixture was heating at 60°-70° C. under stirring, then 3.2 g of N-(2-hydroxyethyl)-N-(4-chlorobutyryl)cyclohexylamine was added dropwise gradually thereto. After the addition operation, the reaction mixture was further stirred at the same temperature for 4 hours. Then the solvent was removed by distillation and the residue thus obtained was dissolved in 200 ml of chloroform and the chloroform layer was washed with a diluted hydrochloric acid, 1% Na OH aqueous solution and water in this order, then dried with anhydrous sodium sulfate. The drying agent was removed by filtration, and the mother liquid was concentrated, then the residue thus obtained was crystallized with petroleum ether. The crystals thus obtained was recrystallized from chloroform-petroleum ether to obtain 0.5 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril. Melting point: 165°-166° C.

後処理

  1. temperatureThe mixture was heating at 60°-70° C.
  2. stirringAfter the addition operation, the reaction mixture was further stirred at the same temperature for 4 hours
  3. customThen the solvent was removed by distillation
  4. customthe residue thus obtained
  5. washthe chloroform layer was washed with a diluted hydrochloric acid, 1% Na OH aqueous solution and water in this order
  6. dry with materialdried with anhydrous sodium sulfate
  7. customThe drying agent was removed by filtration
  8. concentrationthe mother liquid was concentrated
  9. customthe residue thus obtained
  10. customwas crystallized with petroleum ether
  11. customThe crystals thus obtained
  12. customwas recrystallized from chloroform-petroleum ether

出典と根拠

ORDレコード
ord-ada3bb29a2814705928669c25a3fac6b
出典データセット
uspto-grants-1984_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04435404

反応ノート

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