Hydrochloric Acid → 1-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-2-benzimidazolinone

HRID 274942Notes

Reaction equation

HRID 274942 reaction equation
[C:1]([CH:6]([C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17](C(OCC)=O)[C:16]2=[O:29])=[CH:10][C:9]=1[CH2:30][CH2:31][CH3:32])([O:3]CC)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH:6]([C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[NH:17][C:16]2=[O:29])=[CH:10][C:9]=1[CH2:30][CH2:31][CH3:32])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200891921-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone

Product 1

HCID 152317901-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-propylphenylmethyl]-2-benzimidazolinoneYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product of step D (0.132 g, 0.24 mmol) was suspended in 2.0 mL of methanol and the flask was placed in a sonicator bath until the contents were completely dissolved. Next, 95 μL of a 5.0 N solution of sodium hydroxide were added and the reaction was stirred at room temperature overnight. The reaction mixture was then adjusted to pH=5-6 with dropwise addition of 6 N hydrochloric acid, and then concentrated in vacuo. The residue was redissolved in methanol, filtered, and evaporated. The mixture was then purified on a silica gel flash chromatography column eluted with CHCl3 -MeOH-NH4OH (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.038 g (35%) of the title compound.

Workup

  1. customthe flask was placed in a sonicator bath until the contents
  2. dissolutionwere completely dissolved
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was redissolved in methanol
  5. filtrationfiltered
  6. customevaporated
  7. customThe mixture was then purified on a silica gel flash chromatography column
  8. washeluted with CHCl3 -MeOH-NH4OH (80:15:1)
  9. customEvaporation of the purified fractions
  10. customdrying in vacuo

Sources & evidence

ORD record
ord-466b9600710d408c975be59d909d64cb
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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