Acetonitrile → HCID 58653656, compound

HRID 1676027Notes

Reaction equation

HRID 1676027 reaction equation
[N:1]1([CH:10]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)[CH2:11][C:12]([O:14]CC)=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(#N)C>Cl>[N:1]1([CH:10]([C:17]2[CH:18]=[CH:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)[CH2:11][C:12]([OH:14])=[O:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 58653659HCID 58653659, compound

Product 1

HCID 58653656HCID 58653656, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl 3-(1H-benzimidazol-1-yl)-3-(1,1′-biphenyl)-4-ylpropanoate (276 mg, 746 μmol) in hydrochloric acid (50 mL of a 5N solution) was stirred at room temperature for 12 hours. Acetonitrile (I mL) was then added, and stirring continued for 110 hours. The solution was warmed to reflux for 24 hours and was then cooled to room temperature and evaporated in vacuo. The residue was taken up into aqueous sodium carbonate and the resulting solution extracted with diethyl ether. The aqueous phase was acidified with dilute hydrochloric acid (pH<4), and re-extracted with dichloromethane. The combined dichloromethane extracts were evaporated in vacuo, and the residue was recrystallized from methanol to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=4.66 min, MH+ 343].

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 24 hours
  3. customevaporated in vacuo
  4. extractionthe resulting solution extracted with diethyl ether
  5. extractionre-extracted with dichloromethane
  6. customThe combined dichloromethane extracts were evaporated in vacuo
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-7aa690887e78482db0d8a3ae05922af4
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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