3-Bromobenzaldehyde → HCID 136408147, compound

HRID 1519406Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:3]=1[C:4]([NH2:6])=[O:5].[Br:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH:19]=O.OS([O-])=O.[Na+].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[Br:15][C:16]1[CH:17]=[C:18]([C:19]2[NH:6][C:4](=[O:5])[C:3]3[C:2](=[CH:10][C:9]([O:11][CH3:12])=[CH:8][C:7]=3[O:13][CH3:14])[N:1]=2)[CH:21]=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 2-amino-4,6-dimethoxy-benzamide (0.5 g, 2.55 mmol) in N,N-dimethylacetamide (30 mL) was added 3-bromo-benzaldehyde (0.32 mL, 2.80 mmol) followed by NaHSO3 (0.39 g, 3.82 mmol) and p-toluenesulfonic acid monohydrate (0.24 g, 1.27 mmol). The reaction was heated at 120° C. for 20 h. After that time it was cooled to room temperature (rt), concentrated under reduced pressure and diluted with water. The precipitated solids were collected by filtration, washed with water and dried under vacuum. The product was triturated with diethyl ether to give 2-(3-bromo-phenyl)-5,7-dimethoxy-3H-quinazolin-4-one (0.81 g, 88%) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.23 (s, 1H), 7.84 (d, J=7.0 Hz, 1H), 7.66 (d, J=7.0 Hz, 1H), 7.38 (t, J=7.0 Hz, 1H), 6.8 (s, 1H), 6.46 (s, 1H), 3.94 (s, 3H), 3.90 (s, 3H).

Workup

temperatureAfter that time it was cooled to room temperature (rt)
concentrationconcentrated under reduced pressure
additiondiluted with water
filtrationThe precipitated solids were collected by filtration
washwashed with water
customdried under vacuum
customThe product was triturated with diethyl ether

Sources & evidence

ORD record: ord-75dff0b3bf0b44ffa7d2b2d6d97a569e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073878B2

Reaction notes

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