Hydrochloric Acid → [3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-dimethyl-amine

HRID 422538

반응식

HRID 422538 반응식
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1)=O.[CH3:12][NH:13][CH3:14].C=O.Cl.[BH4-].[Na+].C([O-])(O)=O.[Na+].[NH:25]1[CH:29]=[N:28][N:27]=[N:26]1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(O)C.C(OCC)(=O)C>[Cl:11][C:6]1[CH:5]=[C:4]([CH:2]([N:26]2[N:27]=[N:28][CH:29]=[N:25]2)[CH2:1][CH2:12][N:13]([CH3:30])[CH3:14])[CH:9]=[CH:8][C:7]=1[Cl:10]

참가 물질

12

반응물 9

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 712FormaldehydeHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 75841Ethanone, 1-(3,4-dichlorophenyl)-HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 178418441HCID 178418441, 화합물

생성물 1

HCID 49866033[3-(3,4-Dichloro-phenyl)-3-tetrazol-2-yl-propyl]-dimethyl-amine수율 35%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3,4-dichloroacetophenone (2 mmol) in ethanol was added dimethylamine (5 equiv.), paraformaldehyde (5 equiv.) and aq. HCl. After 12 h, the solvent was removed and ethyl acetate and 1N NaOH were added and organic layer was extracted 3 times. It was dried over MgSO4, filtered, evaporated and the filtrate was concentrated at reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate and hexane. The product was dissolved in methanol and added NaBH4 (2 equiv.). After 2 h, sat. NaHCO3 and ethyl acetate were added and the organic layer was extracted 3 times with ethyl acetate. It was dried over MgSO4, filtered, evaporated and the filtrate was concentrated at reduced pressure. The residue was purified by column chromatography eluting with ethyl acetate and methanol. The resulting residue was dissolved in THF and was added 1H-tetrazole (1.5 equiv.), triphenylphosphine (1.5 equiv.) and diisopropyl azodicarboxylate (1.5 equiv.) dropwise at 0□ and warmed to room temperature. After 2 h, the solvent was removed and the residue was purified by column chromatography eluting with ethyl acetate and methanol: Yield 35% 1H-NMR (CDCl3, 200 MHz) d 2.2 (m, 7H), 2.6 (m, 2H), 6.0 (t, 1H), 7.2 (dd, 1H), 7.4 (dd, 1H), 7.5 (d, 1H), 8.5 (s, 1H)

후처리

  1. customthe solvent was removed
  2. additionethyl acetate and 1N NaOH were added
  3. extractionorganic layer was extracted 3 times
  4. dry with materialIt was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. concentrationthe filtrate was concentrated at reduced pressure
  8. customThe residue was purified by column chromatography
  9. washeluting with ethyl acetate and hexane
  10. dissolutionThe product was dissolved in methanol
  11. waitAfter 2 h
  12. extractionthe organic layer was extracted 3 times with ethyl acetate
  13. dry with materialIt was dried over MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. concentrationthe filtrate was concentrated at reduced pressure
  17. customThe residue was purified by column chromatography
  18. washeluting with ethyl acetate and methanol
  19. dissolutionThe resulting residue was dissolved in THF
  20. waitAfter 2 h
  21. customthe solvent was removed
  22. customthe residue was purified by column chromatography
  23. washeluting with ethyl acetate and methanol

출처 및 근거

ORD 기록
ord-7e34e14336684194a24b1b6ee276dc7f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101642B2

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