Sulfuric Acid → methyl 6-amino-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate

HRID 715986ノート

反応式

HRID 715986 の反応式
CC(C)(C)C([NH:5][C:6]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:10]2[N:11]=[C:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:9]2=[CH:8][CH:7]=1)=O.S(=O)(=O)(O)O>CO>[NH2:5][C:6]1[C:17]([C:18]([O:20][CH3:21])=[O:19])=[C:10]2[N:11]=[C:12]3[CH2:16][CH2:15][CH2:14][N:13]3[C:9]2=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 70983330methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate2 回

生成物 1

HCID 86712122methyl 6-amino-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate収率 66.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of methyl 6-(2,2-dimethylpropionylamino)-2,3-dihydro-1Hbenzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (Intermediate 56, 0.61 g) and concentrated sulfuric acid (1.5 mL) in methanol (30 mL) was stirred and heated at reflux for 44 hours. After cooling, the solution was concentrated in vacuo and the residue was dissolved in water and ethyl acetate and basified with 5M sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate (×8) and the combined extracts were dried (Na2SO4) and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ether and filtered to give methyl 6-amino-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (0.296 g) as an off-white solid.

後処理

  1. temperatureheated
  2. temperatureat reflux for 44 hours
  3. temperatureAfter cooling
  4. concentrationthe solution was concentrated in vacuo
  5. dissolutionthe residue was dissolved in water
  6. extractionThe aqueous phase was extracted with ethyl acetate (×8)
  7. dry with materialthe combined extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo
  10. customthe residue was triturated with ether
  11. filtrationfiltered

出典と根拠

ORDレコード
ord-12b7980aee334d7991cb4dd5ba7871ec
出典データセット
uspto-grants-2015_11
特許番号
US09187494B2

反応ノート

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