Pyridine → 1,3-Dibenzyl-5-(phenylacetyl)barbituric acid

HRID 2300040

Reaction equation

[CH2:1]([N:8]1[C:15](=[O:16])[CH2:14][C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:30]1([CH2:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[CH2:1]([N:8]1[C:15](=[O:16])[CH:14]([C:37](=[O:38])[CH2:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:12](=[O:13])[N:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1,3-dibenzyl barbituric acid 192 mg (0.623 mmol) in dry dichloromethane 2.0 mL under nitrogen atmosphere, added was pyridine 1.0 mL (12 mmol) and stirred at 0° C. Added was phenylacetyl chloride 96 mg (0.623 mmol, 1.00 equivalent) in dichloromethane 1.0 mL to the solution slowly during a period of 20 minutes, then stirred at room temperature for 3 hours. Added was dichloromethane 40 mL and washed the organic layer with 2 M hydrochloric acid and saturated brine, and dried over sodium sulfate. Purified was the crude product 273 mg, after removal of the solvent under the reduced pressure, by column chromatography (silica gel, eluted with dichloromethane). It obtained 1,3-dibenzyl-5-(phenylacetyl)barbituric acid 236 mg as colorless viscous oil at first (88.7% yield) and it gradually turned white plates.

Workup

additionAdded
customof 20 minutes
stirringstirred at room temperature for 3 hours
additionAdded
washwashed the organic layer with 2 M hydrochloric acid and saturated brine
dry with materialdried over sodium sulfate
customPurified
customafter removal of the solvent under the reduced pressure
washby column chromatography (silica gel, eluted with dichloromethane)

Sources & evidence

ORD record: ord-dabb582cc5aa4dabb93a2cbe0caa81d9
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06498164B1

Linked notes

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