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

HRID 1066218ノート

反応式

HRID 1066218 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒3 回HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2953f8a6b5d646f2a3ea8e5f780810f3
出典データセット
uspto-grants-2001_06
特許番号
US06242471B1

反応ノート

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