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

HRID 274946
Notes
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Reaction equation

HRID 274946 reaction equation
[C:1]([CH:6]([C:30]1[CH:35]=[CH:34][C:33]2[O:36][CH2:37][O:38][C:32]=2[CH:31]=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][CH:9]=1)([O:3]CC)=[O:2].C(O)C.[OH-].[Na+].Cl>C(Cl)Cl>[C:1]([CH:6]([C:30]1[CH:35]=[CH:34][C:33]2[O:36][CH2:37][O:38][C:32]=2[CH:31]=1)[O:7][C:8]1[CH:9]=[CH:10][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:12][CH:13]=1)([OH:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 200891941-[4-(1-Carboethoxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-3-carboethoxy-2-benzimidazolinone

Product 1

HCID 152317851-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-2-benzimidazolinoneYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with 0.025 g (0.05 mmol) of the product of step C, 0.5 mL of ethanol and the flask and its contents were placed in a sonicator bath. Methylene chloride (0.3 mL) was then added in order to completely dissolve the starting material. Next, 20 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 with dropwise addition of 6 N hydrochloric acid, and then concentrated in vacuo. The residue was suspended in water to dissolve inorganic salts and filtered. The flitrate was washed with methanol and dried in vacuo to afford 0.016 g (80%) of the title compound.

Workup

  1. customthe flask and its contents were placed in a sonicator bath
  2. dissolutionto completely dissolve the starting material
  3. concentrationconcentrated in vacuo
  4. dissolutionto dissolve inorganic salts
  5. filtrationfiltered
  6. washThe flitrate was washed with methanol
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0eaa91c4beed481494f16705c39b709b
Source dataset
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05391566

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes