1-(1,3-Benzodioxol-5-yl)-1-isopropylurea → 1-Isopropyl-6,7-methylenedioxy4-(5-indanyl)-3,4-dihydro-quinazolin-2(1H)-one

HRID 1993317Notes

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

Participants

Reactant 2

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

HCID 1216245-Indanecarboxaldehyde

Product 1

HCID 121501791-Isopropyl-6,7-methylenedioxy4-(5-indanyl)-3,4-dihydro-quinazolin-2(1H)-oneYield 59%

Procedure

This compound was synthesized from N-isopropyl-N-[3,4-(methylenedioxy)-phenyl]urea (291 mg) and 5-indancarboxaldehyde (190 mg) by the procedure described in example 10 in 59% yield, mp: 146-148° C. 1H NMR (CDCl3): 7.21-7.04 (m, 3H), 6.67 (s, 1H), 6.30 (s, 1H), 5.91 (d, J=1.4, 1H), 5.89 (d, J=1.4, 1H), 5.27 (s, 1H), 5.00 (s, 1H), 4.45 (m, 1H), 2.89 (m, 4H), 2.08 (m, 2H), 2.08 (m, 2H), 1.58-1.55 (m, 6H). Anal. calcd. for C21H22N2O3: C, 71.98; H, 6.33; N, 7.99. Found: C, 72.25; H, 6.59; N, 7.89.

Sources & evidence

ORD record: ord-0ffbf112d904425ca69a20ed1b32b732
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652006B2

Reaction notes

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