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

HRID 274937Notes

Reaction equation

HRID 274937 reaction equation
[C:1]([CH:6]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18](C(OCC)=O)[C:17]2=[O:30])=[CH:10][C:9]=1[Cl:31])([O:3]CC)=[O:2].[OH-].[Na+].Cl>CO.C(Cl)Cl>[C:1]([CH:6]([C:32]1[CH:37]=[CH:36][C:35]2[O:38][CH2:39][O:40][C:34]=2[CH:33]=1)[O:7][C:8]1[C:9]([Cl:31])=[CH:10][C:11]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[NH:18][C:17]2=[O:30])=[CH:12][C:13]=1[Cl:14])([OH:3])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20089200HCID 20089200, compound

Product 1

HCID 152317831-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dichlorophenylmethyl]-2-benzimidazolinoneYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.082 g (0.14 mmol) of the product of step C in 1.0 mL of methanol and 1.0 mL methylene chloride was added 250 gL of a 5.0 N solution of sodium hydroxide and the reaction was stirred at room temperature for 16 hours. 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 0.061 g (90%) 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
  7. customEvaporation of the purified fractions
  8. customdrying in vacuo

Sources & evidence

ORD record
ord-af11c9a226ca41adb00844352736a9cc
Source dataset
uspto-grants-1995_02
Patent number
US05391566

Reaction notes

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