Hydrochloric Acid → 1-[4-(1-Carboxy-1-(3,4-methylenedioxyphenyl)methoxy)phenylmethyl]-2-benzimidazolinone
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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- customthe flask and its contents were placed in a sonicator bath
- dissolutionto completely dissolve the starting material
- concentrationconcentrated in vacuo
- dissolutionto dissolve inorganic salts
- filtrationfiltered
- washThe flitrate was washed with methanol
- customdried in vacuo
Sources & evidence
- ORD record
- ord-0eaa91c4beed481494f16705c39b709b
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05391566
Reaction notes
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