Sodium Hydroxide → Ethyl 4,5-dihydro-8-methylthio-2-phenylthieno(3,4-e]benzimidazole-6-carboxylate

HRID 1936871노트

반응식

HRID 1936871 반응식
[OH-].[Na+].Cl.[C:4]([NH2:12])(=[NH:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH:14]1[CH2:29][CH2:28][C:17]2=[C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:19][C:20]([S:21][CH3:22])=[C:16]2[C:15]1=O>O.C(Cl)(Cl)Cl>[CH3:22][S:21][C:20]1[S:19][C:18]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]2[CH2:28][CH2:29][C:14]3[N:11]=[C:4]([C:5]4[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=4)[NH:12][C:15]=3[C:16]=12

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 80289Benzamidine, hydrochlorideHCID 15885619Ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate

생성물 1

HCID 178470566Ethyl 4,5-dihydro-8-methylthio-2-phenylthieno(3,4-e]benzimidazole-6-carboxylate수율 13.2%

시약·촉매·용매 2

HCID 962Water용매3회HCID 6212Chloroform용매

실험 절차

A solution of sodium hydroxide (1.65 g) in water (3 ml) was added to a solution of benzamidine hydrochloride (5.38 g) in water (2 ml) at room temperature; a solution of ethyl 5-bromo-4,5,6,7-tetrahydro-3-methylthio-4-oxobenzo[c]thiophene-1-carboxylate (2.00 g) in chloroform (30 ml) was further added. The reaction mixture was refluxed under heating for 3 days, after which it was poured over water and extracted with ethyl acetate. The organic layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane (1:2, v/v) to yield ethyl 4,5-dihydro-8-methylthio-2-phenylthieno[3,4-e]benzimidazole-6-carboxylate (0.28 g, 13.2%), which was then recrystallized from ethyl acetate-ethanol. Brown prisms. Melting point 218-219° C.

후처리

  1. temperatureThe reaction mixture was refluxed
  2. temperatureunder heating for 3 days
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationafter which the solvent was distilled off
  7. washeluted with ethyl acetate-hexane (1:2

출처 및 근거

ORD 기록
ord-28b72e3403d84733a78faffe6a195e5e
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391905B1

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