1-(1,3-Benzodioxol-5-yl)-1-isopropylurea → 1-Isopropyl-6,7-methylenedioxy-4-(3,4-ethylenedioxi-phenyl)-3,4-dihydroquinazolin-2(1H)-one

HRID 1884370Notes

Reaction equation

HRID 1884370 reaction equation
[CH:1]([N:4]([C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1)[C:5]([NH2:7])=[O:6])([CH3:3])[CH3:2].[O:17]1[C:22]2[CH:23]=[CH:24][C:25]([CH:27]=O)=[CH:26][C:21]=2[O:20][CH2:19][CH2:18]1>>[CH:1]([N:4]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH:27]([C:25]2[CH:24]=[CH:23][C:22]3[O:17][CH2:18][CH2:19][O:20][C:21]=3[CH:26]=2)[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1005551-(1,3-Benzodioxol-5-yl)-1-isopropylureaHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehyde

Product 1

HCID 121501731-Isopropyl-6,7-methylenedioxy-4-(3,4-ethylenedioxi-phenyl)-3,4-dihydroquinazolin-2(1H)-oneYield 32%

Procedure

This compound was synthesized from N-isopropyl-N-[3,4-(methylenedioxy)-phenyl]urea (240 mg) and 1,4-benzodioxan-6-carboxaldehyde (181 mg) by the procedure described in example 10 in 32% yield, mp: 185-187° C. 1H NMR (CDCl3): 6.86-6.75 (m, 3H), 6.67 (s, 1H), 6.30 (s, 1H), 5.91 (s, 1H), 6.89 (s, 1H), 5.18 (s, 1H), 4.99 (br s, 1H), 4.44 (m, 2H), 4.25 (s, 4H), 1.56 (d, J=6.8, 3H), 1.55 (d, J=6.8, 3H). Anal. calcd. for C20H20N2O5.(½)H2O: C, 63.65; H, 5.61; N, 7.42. Found: C. 63.37; H, 5.34; N, 7.07.

Sources & evidence

ORD record
ord-6dba3fd51d624eddbd3024d148866825
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

Loading…