Hydrochloric Acid → HCID 19689870, compound

HRID 2465Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH2:30][CH:31]1OCC[O:32]1)[C:10](=[O:29])[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[CH:13][CH:12]=1.Cl>C1COCC1>[CH:31]([CH2:30][N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:10](=[O:29])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][N:18]2[C:22](=[O:23])[C:21]3=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]3[C:19]2=[O:28])=[CH:15][CH:16]=1)=[O:32]

Participants

Conditions

Temperature: 60 °C

Procedure

N-(2-Methoxyphenyl)-N-(1,3-dioxolan-2-yl)methyl-4-phthalimidomethylbenzamide (450 mg, 0.953 mmol) was dissolved in THF (6 ml) to which was subsequently added 10% hydrochloric acid (4 ml) at room temperature. After 2 hours of stirring at 60° C., the resulting reaction solution was extracted with chloroform and washed with saturated brine. The resulting organic layer was dried on anhydrous magnesium sulfate, the solvent was removed by evaporation and then the resulting residue was mixed with 5 ml of chloroform to remove insoluble materials by filtration, thereby obtaining 300 mg (73.5%) of the title compound in the form of yellow oil which was used in the subsequent reaction without further purification.

Workup

customat room temperature
customthe resulting reaction solution
extractionwas extracted with chloroform
washwashed with saturated brine
dry with materialThe resulting organic layer was dried on anhydrous magnesium sulfate
customthe solvent was removed by evaporation
additionthe resulting residue was mixed with 5 ml of chloroform
customto remove insoluble materials
filtrationby filtration

Sources & evidence

ORD record: ord-6f48f4894ab44bc5ac2137804fdccac1
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05728835

Reaction notes

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