Methanol → HCID 11609036, compound

HRID 1676025Notes

Reaction equation

HRID 1676025 reaction equation
[N:1]1([CH:10]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[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.CO>Cl>[N:1]1([CH:10]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[CH:19][CH:18]=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

5

Reactant 3

HCID 887MethanolHCID 6342AcetonitrileHCID 58653653HCID 58653653, compound

Product 1

HCID 11609036HCID 11609036, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of ethyl 3-(1H-benzimidazol-1-yl)-3-(4-ethylphenyl)propanoate (180 mg, 559 μmol) in hydrochloric acid (10 mL of a 5N solution) was stirred at room temperature for 72 hours. A mixture of acetonitrile and methanol (10:1, 11 mL) was added, and the resulting solution stirred at room temperature for 110 hours. The solution was warmed to reflux for 24 hours, 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 extracted with dichloromethane. The combined dichloromethane extracts were evaporated in vacuo to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=4.20 min, MH+ 296].

Workup

  1. additionwas added
  2. stirringthe resulting solution stirred at room temperature for 110 hours
  3. temperatureThe solution was warmed
  4. temperatureto reflux for 24 hours
  5. customevaporated in vacuo
  6. extractionthe resulting solution extracted with diethyl ether
  7. extractionextracted with dichloromethane
  8. customThe combined dichloromethane extracts were evaporated in vacuo

Sources & evidence

ORD record
ord-75243292c9184fa4b9f402c5ecbaf9fe
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

Loading…