Hydrochloric Acid → HCID 178468511, compound

HRID 1291009Notes

Reaction equation

HRID 1291009 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([OH:13])=[O:12])=[CH:8][C:7]=2[CH:14]=1)#[N:2].[ClH:15].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:24](O)[CH3:25]>>[ClH:15].[CH2:16]([NH:23][C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([O:13][CH2:24][CH3:25])=[O:12])=[CH:8][C:7]=2[CH:14]=1)=[NH:2])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7504BenzylamineHCID 102360545-cyanobenzofuran-2-carboxylic Acid

Product 1

HCID 178468511HCID 178468511, compoundYield 30%

Procedure

Ethanol (30 ml) was added to 5-cyano-2-benzofurancarboxylic acid (689 mg, 3.68 mmol) and a hydrogen chloride gas was blown in under ice-cooling for 15 minutes and the mixture was stirred at room temperature for 16 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure and the residue was dissolved in ethanol (25 ml). Benzylamine (1.58 g, 14.7 mmol) was added under ice-cooling and the mixture was stirred for one hour and at room temperature for 2 hours. Low boiling matters were distilled away from the reaction mixture under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=100/3-4/1) to give 361 mg of ethyl 5-benzylamidino-2-benzofurancarboxylate hydrochloride as a colorless solid (30%).

Workup

  1. temperaturecooling for 15 minutes
  2. distillationwere distilled away from the reaction mixture under reduced pressure
  3. dissolutionthe residue was dissolved in ethanol (25 ml)
  4. temperaturecooling
  5. stirringthe mixture was stirred for one hour and at room temperature for 2 hours
  6. distillationwere distilled away from the reaction mixture under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/3-4/1)

Sources & evidence

ORD record
ord-a2ca053215194952b4e9d2790583901d
Source dataset
uspto-grants-1998_05
Patent number
US05753670

Reaction notes

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