Water → 1,3-bis[4-(2-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione

HRID 6182

Reaction equation

[CH:1]1[CH:6]=[C:5]2[C:7]([NH:9][C:10]([NH:12][C:4]2=[CH:3][CH:2]=1)=[O:11])=[O:8].Cl[CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.[CH2:25]1[CH2:35][CH2:34][N:33]2C(=NC[CH2:31][CH2:32]2)CC1.O>CN(C)C=O>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[S:18][CH2:17][CH2:16][CH2:15][CH2:14][N:12]1[C:4]2[C:5](=[CH:6][CH:1]=[CH:2][CH:3]=2)[C:7](=[O:8])[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][S:18][C:32]2[CH:31]=[CH:25][CH:35]=[CH:34][N:33]=2)[C:10]1=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1.62 g (10 mmol) of benzoylene urea and 2.02 g (10 mmol) of 2-(4-chlorobutylthio)pyridine in 50 ml of dimethylformamide, 1.65 ml (11 mmol) of 1,8-diazabicyclo[5.4.0]-7-undecene was added, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the solvent was distilled off. The residue was purified by column chromatography (eluent: hexane/ethyl acetate =2:1 to 1:2). First, 221 mg of the desired product was obtained (4.6% yield, yellow oil), and then, 292 mg of 3-[4-(2-pyridylthio)butyl]quinazoline-2,4(1H,3H)-dione was obtained (8.9% yield, white crystals).

Workup

temperatureAfter cooling
extractionthe mixture was extracted with ethyl acetate
customThe extract was dried
distillationthe solvent was distilled off
customThe residue was purified by column chromatography (eluent: hexane/ethyl acetate =2:1 to 1:2)

Sources & evidence

ORD record: ord-9bc7f16969ba4b2985a63d53dcd01956
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05246948

Linked notes

Loading…