Hydrochloric Acid → 1-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-chloro-5-propylphenylmethyl]-2-benzimidazolinone

HRID 274935Notes

Reaction equation

HRID 274935 reaction equation
[C:1]([CH:5]([C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[O:6][C:7]1[C:12]([CH2:13][CH2:14][CH3:15])=[CH:11][C:10]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19](C(OCC)=O)[C:18]2=[O:31])=[CH:9][C:8]=1[Cl:32])([O:3]C)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH:5]([C:33]1[CH:38]=[CH:37][C:36]2[O:39][CH2:40][O:41][C:35]=2[CH:34]=1)[O:6][C:7]1[C:12]([CH2:13][CH2:14][CH3:15])=[CH:11][C:10]([CH2:16][N:17]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[NH:19][C:18]2=[O:31])=[CH:9][C:8]=1[Cl:32])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200891971-[4-(1-Carbomethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-chloro-5-propylphenylmethyl]-3-carboethoxy-2-benzimidazolinone

Product 1

HCID 152317821-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3-chloro-5-propylphenylmethyl]-2-benzimidazolinoneYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.088 g (0.15 mmol) of the product of step F in 4 mL of methanol was added 250 μL of a 5.0 N solution of sodium hydroxide and the reaction was stirred at room temperature for 2 hours. The reaction mixture was then adjusted to pH=6 with dropwise addition of 2 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 (51%) of the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was redissolved in methanol
  3. filtrationfiltered
  4. customevaporated
  5. customThe mixture was then purified on a silica gel flash chromatography column
  6. washeluted with CHCl3 -MeOH-NH4OH (80:15:1)
  7. customEvaporation of the purified fractions
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-cb54b3f108d347eea97ddc12672a54fc
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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