1,2-Dichloroethane → 2,3-dihydroindol-1-yl(4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanone

HRID 1440044Notes

Reaction equation

HRID 1440044 reaction equation
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.Cl[CH2:23][CH2:24]Cl>>[N:6]1([C:15]([CH:13]2[CH2:12][CH2:11][C:10]3[N:6]=[CH:7][NH:8][C:9]=3[CH2:14]2)=[O:17])[C:23]2[C:24](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 148567954,5,6,7-Tetrahydrobenzimidazole-5-carboxylic acid sulfate

Product 1

HCID 1329642,3-dihydroindol-1-yl(4,5,6,7-tetrahydro-3H-benzimidazol-5-yl)methanoneYield 82.7%

Conditions

Temperature
30 °C

Procedure

4,5,6,7-Tetrahydrobenzimidazole-5-carboxylic acid sulfate (1.32 g) was refluxed in 10 ml of 1,2-dichloroethane together with 1.78 g of thionyl chloride for 30 minutes, and the excess of thionyl chloride and the solvent were removed by distillation under reduced pressure. To the residue was added ml of 1,2-dichloroethane, and 1.6 ml of indoline was added dropwise thereto at 30° C. or lower while stirring followed by stirring at room temperature for 2 hours. The reaction mixture was successively extracted once with 30 ml of water and twice with 20 ml of water. The combined aqueous layer was adjusted to a pH of 9 to 10 with a 10% sodium hydroxide aqueous solution and then extracted with methylene chloride. The combined methylene chloride layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 1.1 g (82.7%) of 5-[(2,3-dihydroindol-1-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole.

Workup

  1. customthe excess of thionyl chloride and the solvent were removed by distillation under reduced pressure
  2. additionTo the residue was added ml of 1,2-dichloroethane, and 1.6 ml of indoline
  3. additionwas added dropwise
  4. stirringby stirring at room temperature for 2 hours
  5. extractionThe reaction mixture was successively extracted once with 30 ml of water and twice with 20 ml of water
  6. extractionextracted with methylene chloride
  7. washThe combined methylene chloride layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4fc35d26f0c04b22924aaedb63b0094a
Source dataset
uspto-grants-1996_03
Patent number
US05496942

Reaction notes

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