p-Toluenesulfonic acid → HCID 70876732, compound

HRID 1846267Notes

Reaction equation

[NH2:1][C:2]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:9][CH:8]=1)=[O:5].[CH3:22][C:23]1[CH:24]=[C:25]([CH:28]=[C:29]([CH3:35])[C:30]=1[O:31][CH2:32][CH2:33][OH:34])[CH:26]=O.S(=O)(O)[O-].[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C(=O)C>[CH:13]([C:10]1[CH:9]=[CH:8][C:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:20][C:19]([F:21])=[CH:18][CH:17]=3)[NH:1][CH:26]2[C:25]2[CH:28]=[C:29]([CH3:35])[C:30]([O:31][CH2:32][CH2:33][OH:34])=[C:23]([CH3:22])[CH:24]=2)=[CH:12][CH:11]=1)([CH2:15][CH3:16])[CH3:14]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-amino-N-(4-sec-butyl-phenyl)-4-fluoro-benzamide (0.920 g, 3.21 mmol), 3,5-dimethyl-4-(2-hydroxy-ethoxy)-benzaldehyde (0.627 g, 3.21 mmol), sodium bisulfite (0.640 g, 3.53 mmol), and p-toluenesulfonic acid (60 mg, 0.32 mmol) in N,N-dimethylacetamide (20 mL) was heated at 120° C. for 16 hours. The solvent was evaporated in vacuo and water was added to the flask. The precipitate was filtered off and washed with water. The solid was triturated with ether and filtered off to give 3-(4-sec-butyl-phenyl)-7-fluoro-2-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-2,3-dihydro-1H-quinazolin-4-one (P) (0.11 g). The filtrate was evaporated under vacuum to give second crop of (1.02 g). The combined yield: 1.13 g (quantitative).

Workup

customThe solvent was evaporated in vacuo and water
additionwas added to the flask
filtrationThe precipitate was filtered off
washwashed with water
customThe solid was triturated with ether
filtrationfiltered off

Sources & evidence

ORD record: ord-83afd4185d0c4459bf4d2315081c4683
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952021B2

Reaction notes

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