Benzamidine, hydrochloride → HCID 22386595, compound

HRID 1067486Notes

Reaction equation

HRID 1067486 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

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 517045Sodium AcetateHCID 27374532-fluoro-6-phenoxybenzonitrile

Product 1

HCID 22386595HCID 22386595, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

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

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

Sources & evidence

ORD record
ord-d5c49d7d92964d64adc7a7aae71dcb94
Source dataset
uspto-grants-2001_06
Patent number
US06248771B1

Reaction notes

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