Methanesulfonic Acid → 3,4-Dihydroquinazolin-2(1H)-one

HRID 445179Notes

Reaction equation

HRID 445179 reaction equation
COC1C=CC([N:9]([C:13]2[CH:18]=[CH:17][C:16](OC)=[CH:15][CH:14]=2)[C:10]([NH2:12])=[O:11])=CC=1.[CH3:21]S(O)(=O)=O>COCCOCCOC>[NH:9]1[C:13]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:21][NH:12][C:10]1=[O:11]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 222639891,1-Bis-(4-methoxy-phenyl)-urea

Product 1

HCID 123607563,4-Dihydroquinazolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

A solution of 144 mg (0.53 mmol) 1,1-bis-(4-methoxy-phenyl)-urea, 160 μl (1.06 mmol) cumic aldehyde and 16 μl (0.27 mmol) methane sulfonic acid in 1 ml diglyme is heated for 4 d at 100°. The reaction mixture is extracted with water/dichloromethane and the intermediate dihydro-quinazolinone is isolated by preparative HPLC. Oxidation with ruthenium trichloride and sodium periodate, as described above, furnishes 4-(4-isospropyl-phenyl)-6-methoxy-1-(4-methoxy-phenyl)-1.H.-quinazolin-2-one.

Workup

  1. extractionThe reaction mixture is extracted with water/dichloromethane

Sources & evidence

ORD record
ord-d66c81a8b89a46ef8f5750e4ec0352b3
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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