1-(1,3-Benzodioxol-5-yl)-1-isopropylurea → 1-Isopropyl-6,7-methylenedioxy-4-(2-chloro-4,5-methylenedioxyphenyl)-3,4-dihydro-quinazolin-2(1h)-one

HRID 1884375Notes

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].[CH2:17]1[O:21][C:20]2[CH:22]=[C:23]([Cl:28])[C:24]([CH:26]=O)=[CH:25][C:19]=2[O: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:26]([C:24]2[CH:25]=[C:19]3[O:18][CH2:17][O:21][C:20]3=[CH:22][C:23]=2[Cl:28])[NH:7][C:5]1=[O:6])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 1005551-(1,3-Benzodioxol-5-yl)-1-isopropylurea

HCID 1400146-Chloropiperonal

Product 1

HCID 121501801-Isopropyl-6,7-methylenedioxy-4-(2-chloro-4,5-methylenedioxyphenyl)-3,4-dihydro-quinazolin-2(1h)-oneYield 65%

Procedure

This compound was synthesized from N-isopropyl-N-[3.4-(methylenedioxy)-phenyl]urea (410 mg) and 6-chloropiperonal (350 mg) by the procedure described in example 10 in 65% yield. 1H NMR (CDCl3): 6.86 (s, 1H), 6.77 (s, 1H), 6.48 (s, 1H), 6.40 (s, 1H), 5.95 (s, 4H), 5.66 (d, J=2.5, 1H), 5.21 (s, 1H), 4.48 (m, 1H), 1.53 (d, J=6.5, 6H).

Sources & evidence

ORD record: ord-0195ba5497f04fe6abe4c16bc9422980
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06765006B2

Reaction notes

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