p-Toluenesulfonic acid → 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one

HRID 591632Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[C:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12].CC1C=CC(S(O)(=O)=O)=CC=1.OS([O-])=O.[Na+]>CC(N(C)C)=O>[C:11]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:27]=[CH:26][C:23]([C:24]3[NH:6][C:4](=[O:5])[C:3]4[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:1]=3)=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)(=[O:13])[CH3:12]

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 2-aminobenzamide (1.0 g, 7.35 mmol) and 4-(4-acetylpiperazin-1-yl)benzaldehyde (1.71 g, 7.35 mmol) in DMA (60 mL) was added p-TsOH (0.140 g, 0.73 mmol) and NaHSO3 (0.841 g, 8.1 mmol). The reaction mixture was heated at 150° C. for 21 hours, concentrated to half-volume, diluted with water (300 mL), extracted with CH2Cl2 (2×200 mL), washed with brine (200 mL), dried over anhydrous MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography, eluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH), to afford 2-(4-(4-acetylpiperazin-1-yl)phenyl)quinazolin-4(3H)-one as a yellow solid (2.27 g, 89%).

Workup

concentrationconcentrated to half-volume
additiondiluted with water (300 mL)
extractionextracted with CH2Cl2 (2×200 mL)
washwashed with brine (200 mL)
dry with materialdried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with 100% CH2Cl2 to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH)

Sources & evidence

ORD record: ord-10d89f78bb49442ea62802f98ed57985
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238640B2

Reaction notes

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