Hydrochloric Acid → HCID 66759669, compound

HRID 1402793Notes

Reaction equation

HRID 1402793 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:17][C:18](=O)[CH2:19][CH:20]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)[CH2:21][C:22]([OH:24])=[O:23])([O-])=O.Cl.[C:34]([O-])(O)=O.[Na+].C(OCC)(=O)C>CO.Cl.[Fe]>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH:20]([CH2:19][C:18]2[NH:1][C:4]3[CH:9]=[C:8]([O:10][C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:7]=[CH:6][C:5]=3[N:17]=2)[CH2:21][C:22]([O:24][CH3:34])=[O:23])=[CH:26][CH:27]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66759560HCID 66759560, compound

Product 1

HCID 66759669HCID 66759669, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

N-(2-Nitro-4-phenoxyphenyl)-3-(4-chlorophenyl)glutaramic acid (0.72 g) is dissolved in methanol (8 ml). Iron powder (0.88 g) is added and the suspension is heated to reflux. Conc. HCl (10 drops) was added carefully and refluxing was continued for 1 h. Then further conc. HCl (4 ml) was added and the greenish-yellow solution was stirred at reflux for additional 20 h. After cooling to rt the solution was poured into a mixture of sat. NaHCO3 solution (60 ml) and ethyl acetate (50 ml). The inorganic precipitates were removed by suction filtration and subsequently washed with ethyl acetate. From the filtrate the organic layer was separated and the aqueous layer extracted with ethyl acetate (50 ml). The combined organic layers were dried (sodium sulfate), concentrated and dried in vacuo. The residue (0.61 g of brownish oil) was purified by flash chromatography (dichloromethane/2% methanol/1% triethyl amine) on silica gel to give methyl 3-(4-chlorophenyl)-4-(5-phenoxy-2-benzimidazolyl)butanoate (0.46 g) as a colourless solid.

Workup

  1. temperaturethe suspension is heated to reflux
  2. temperaturerefluxing
  3. temperatureat reflux for additional 20 h
  4. customThe inorganic precipitates
  5. customwere removed by suction filtration
  6. washsubsequently washed with ethyl acetate
  7. customFrom the filtrate the organic layer was separated
  8. extractionthe aqueous layer extracted with ethyl acetate (50 ml)
  9. dry with materialThe combined organic layers were dried (sodium sulfate)
  10. concentrationconcentrated
  11. customdried in vacuo
  12. customThe residue (0.61 g of brownish oil) was purified by flash chromatography (dichloromethane/2% methanol/1% triethyl amine) on silica gel

Sources & evidence

ORD record
ord-1717e5bda3834c3c9bbaa15f2f9f3582
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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