Dimethylamine → HCID 19600065、化合物

HRID 611303ノート

反応式

HRID 611303 の反応式
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1.[CH2:27]([N:29]([CH2:32]C)[CH2:30]C)C.C(P(=O)(OCC)OCC)#N.CNC.C=O>ClCCl>[CH3:27][N:29]([CH2:32][C:3]1[O:2][C:10]2[CH2:9][CH2:8][N:7]([C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([C:16](=[O:17])[C:11]4[S:15][CH:14]=[CH:13][CH:12]=4)=[CH:19][CH:20]=3)[CH2:6][C:5]=2[CH:4]=1)[CH3:30]

参加物

8

反応物 6

HCID 674DimethylamineHCID 712FormaldehydeHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochlorideHCID 196000994-(2-Thenoyl)benzoic acid

生成物 1

HCID 19600065HCID 19600065、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.279 g (1.2 mmol) of 4-(2-thenoyl)benzoic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. After the solvent was distilled off, water was added, followed by 2 extractions with ethyl acetate. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was dissolved in 10 ml of acetic acid; 0.135 ml (1.50 mmol) of 50% aqueous dimethylamine and 0.122 ml (1.50 mmol) of 37% aqueous formaldehyde were added, followed by stirring at 100° C. for 30 minutes. After the solvent was distilled off under reduced pressure, the residual solution was alkalified with 5% aqueous sodium hydrogen carbonate and extracted with ethyl acetate 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1). The resulting purified product was recrystallized from ethyl acetate-hexane to yield the desired product.

後処理

  1. temperaturecooling
  2. distillationAfter the solvent was distilled off
  3. additionwater was added
  4. extractionfollowed by 2 extractions with ethyl acetate
  5. washThe combined organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. dissolutionThe resulting crude product was dissolved in 10 ml of acetic acid
  9. stirringby stirring at 100° C. for 30 minutes
  10. distillationAfter the solvent was distilled off under reduced pressure
  11. extractionextracted with ethyl acetate 2 times
  12. washThe combined organic layer was washed with water
  13. dry with materialdried over anhydrous sodium sulfate
  14. distillationthe solvent was distilled off under reduced pressure
  15. customThe resulting crude product was purified by silica gel column chromatography (ethyl acetate/methanol=5/1)
  16. customThe resulting purified product
  17. customwas recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-5a04089fa709499d837ff6d5ac5a6a23
出典データセット
uspto-grants-1999_12
特許番号
US05998433

反応ノート

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