Benzamidine, hydrochloride → HCID 22386595, compound

HRID 2121823Notes

Reaction equation

F[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[C:4]#[N:5].Cl.[C:18]([NH2:26])(=[NH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])(=O)C.[Na+]>CN(C)C(=O)C>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][C:6]=2[O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:26]=[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-fluoro-6-phenoxybenzonitrile (2.7 g, 13 mmol), benzamidine hydrochloride (Aldrich) (3.0 g, 19 mmol) and sodium acetate (1.6 g, 19 mmol) in 60 ml of N,N-dimethylacetamide was heated at 150° C. under nitrogen for 6.5 hours. After cooling to room temperature the reaction mixture was evaporated under reduced pressure. The product was suspended in 20 ml of ethanol and water (100 ml) and concentrated ammonium hydroxide (10 ml) was added. The precipitate was isolated by filtration, washed with water, dried and recrystallized twice from 60 ml of 2-propanol at 4° C. The precipitate was collected by filtration, washed with 2-propanol and dried at 50° C. in vacuo to give 4-amino-2-phenyl-5-phenoxyquinazoline (0.5 g, 12%, m.p. 190-191° C.):

Workup

temperatureAfter cooling to room temperature the reaction mixture
customwas evaporated under reduced pressure
additionwater (100 ml) and concentrated ammonium hydroxide (10 ml) was added
customThe precipitate was isolated by filtration
washwashed with water
customdried
customrecrystallized twice from 60 ml of 2-propanol at 4° C
filtrationThe precipitate was collected by filtration
washwashed with 2-propanol
customdried at 50° C. in vacuo

Sources & evidence

ORD record: ord-e7493d85b9fc498a9a97e7630229fc07
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696482B2

Reaction notes

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