Acetonitrile → 5-[(2-Methylbenzofuran-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole fumarate

HRID 1440045ノート

反応式

HRID 1440045 の反応式
S(O)(O)(=O)=O.[N:6]1[C:10]2[CH2:11][CH2:12][CH:13]([C:15]([OH:17])=O)[CH2:14][C:9]=2[NH:8][CH:7]=1.S(Cl)(Cl)=O.[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[C:30]([O-:37])(=O)/[CH:31]=[CH:32]/[C:33]([O-])=O.[C:38](#N)[CH3:39]>C(Cl)(Cl)Cl.CO>[C:22]([OH:29])(=[O:28])/[CH:23]=[CH:24]/[C:25]([OH:27])=[O:26].[CH3:24][C:23]1[O:37][C:30]2[CH:31]=[CH:32][CH:33]=[CH:39][C:38]=2[C:22]=1[C:15]([CH:13]1[CH2:12][CH2:11][C:10]2[N:6]=[CH:7][NH:8][C:9]=2[CH2:14]1)=[O:17]

参加物

7

反応物 5

HCID 6342AcetonitrileHCID 24386Thionyl ChlorideHCID 444972Fumaric AcidHCID 5460307FumarateHCID 148567954,5,6,7-Tetrahydrobenzimidazole-5-carboxylic acid sulfate

生成物 1

HCID 189852385-[(2-Methylbenzofuran-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole fumarate

試薬・触媒・溶媒 1

HCID 21584188Chloroform methanol溶媒

反応条件

温度
55 °C

実験手順

In 40 ml of acetonitrile was suspended 5.00 g of 4,5,6,7-tetrahydrobenzimidazole-5-carboxylic acid sulfate, and 2.75 ml of thionyl chloride was added to the suspension. The suspension was stirred at 55° C. for 1 hour, and the solvent was distilled off under reduced pressure. To the residue was added 20 ml of nitrobenzene and 1.80 ml of 2-methylbenzofurane, and 2.20 ml of tin tetrachloride was then added thereto. After stirring at 85° C. for one night, 40 ml of 1M aqueous hydrochloric acid solution and 40 ml of ethyl ether were added thereto. The organic layer was removed, 40 ml of chloroform was added and then the solution was adjusted to a pH of 9 with 10% aqueous solution of sodium hydroxide. The reaction solution was filtered through celite and then extracted with chloroform containing 10% methanol. The organic layer was collected and the solvent was distilled off. To the free base of objective product obtained by treating the residue with silica gel column chromatography using chloroform/methanol was added calculated amount of fumaric acid to convert it to a fumarate and recrystallized from ethanol to obtain 0.14 g of 5-[(2-methylbenzofuran-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole fumarate.

後処理

  1. additionwas added to the suspension
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the residue was added 20 ml of nitrobenzene and 1.80 ml of 2-methylbenzofurane, and 2.20 ml of tin tetrachloride
  4. additionwas then added
  5. stirringAfter stirring at 85° C. for one night
  6. addition40 ml of 1M aqueous hydrochloric acid solution and 40 ml of ethyl ether were added
  7. customThe organic layer was removed
  8. addition40 ml of chloroform was added
  9. filtrationThe reaction solution was filtered through celite
  10. extractionextracted with chloroform containing 10% methanol
  11. customThe organic layer was collected
  12. distillationthe solvent was distilled off
  13. customTo the free base of objective product obtained
  14. additionby treating the residue with silica gel column chromatography
  15. additionwas added
  16. customrecrystallized from ethanol

出典と根拠

ORDレコード
ord-b5745c3490ab40cd8ea4cd84ddf7549d
出典データセット
uspto-grants-1996_03
特許番号
US05496942

反応ノート

読み込み中…