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Sodium Bicarbonate → 4,5-Bis(4-methoxyphenyl)-2-(3-pyridylacetylaminomethyl)thiazole hydrochloride

HRID 1885564
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HRID 1885564 반응식
[ClH:1].[NH2:2][CH2:3][C:4]1[S:5][C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[N:8]=1.C(=O)([O-])O.[Na+].Cl.CN(C)CCCN=C=NCC.Cl.[N:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][C:50](O)=[O:51])[CH:44]=1>CN(C)C=O.O.ClCCl>[ClH:1].[CH3:16][O:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[N:8]=[C:4]([CH2:3][NH:2][C:50](=[O:51])[CH2:49][C:45]3[CH:44]=[N:43][CH:48]=[CH:47][CH:46]=3)[S:5][C:6]=2[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)=[CH:14][CH:13]=1
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참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 197488812-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride

생성물 1

HCID 197488914,5-Bis(4-methoxyphenyl)-2-(3-pyridylacetylaminomethyl)thiazole hydrochloride수율 39.1%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

2-Aminomethyl-4,5-bis(4-methoxyphenyl)thiazole hydrochloride (1.00 g) was added to a mixture of dichloromethane and saturated aqueous solution of sodium hydrogencarbonate, and was extracted with dichloromethane. The organic layer was washed with water, and brine, and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and resulting residue was dissolved in dimethylformamide (25 ml). To the resulting mixture was added 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride (0.64 g) and 3-pyridylacetic acid hydrochloride (0.52 g), and stirred at ambient temperature for 2 hours and stirred at 60° C. for 5 hours. After allowing to cool to ambient temperature, the mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, water, and brine, and dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The residue was subjected to column chromatography on silica gel (50 g) and eluted with a mixture of methanol and chloroform. The fractions containing the object compound were combined and evaporated in vacuo, and the resulting residue was dissolved in ethanol, and added an ethanol solution of hydrogen chloride. The mixture was evaporated in vacuo, and the resulting precipitate was collected by filtration and washed with diethyl ether, to give 4,5-bis(4-methoxyphenyl)-2-(3-pyridylacetylaminomethyl)-thiazole hydrochloride (0.52 g).

후처리

  1. extractionwas extracted with dichloromethane
  2. washThe organic layer was washed with water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated in vacuo
  6. customresulting residue
  7. stirringstirred at 60° C. for 5 hours
  8. temperatureto cool to ambient temperature
  9. extractionextracted with ethyl acetate
  10. washThe organic layer was washed with saturated aqueous solution of sodium hydrogencarbonate, water, and brine
  11. dry with materialdried over magnesium sulfate
  12. additiontreated with activated charcoal
  13. filtrationAfter filtration
  14. customthe filtrate was evaporated in vacuo
  15. washeluted with a mixture of methanol and chloroform
  16. additionThe fractions containing the object compound
  17. customevaporated in vacuo
  18. dissolutionthe resulting residue was dissolved in ethanol
  19. additionadded an ethanol solution of hydrogen chloride
  20. customThe mixture was evaporated in vacuo
  21. filtrationthe resulting precipitate was collected by filtration
  22. washwashed with diethyl ether

출처 및 근거

ORD 기록
ord-09ec60c8c04e4d01b3385f99bfe4e799
출처 데이터셋
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05145860

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