Benzamidine, hydrochloride → HCID 22386595, compound

HRID 1532627Notes

Reaction equation

HRID 1532627 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, Maybridge), benzamidine hydrochloride (3.0 g, 19 mmol, Aldrich) 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 a mixture of 20 mL of ethanol and 100 mL of water, and 10 mL of concentrated ammonium hydroxide was added. The solid was collected by vacuum filtration, washed with water, dried, recrystallized twice from 60 mL of 2-propanol at 4° C., and dried at 50° C. under vacuum to give 0.5 g (12% yield) of 4-amino-2-phenyl-5-phenoxyquinazoline, m.p. 190-191° C.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas evaporated under reduced pressure
  3. additionThe product was suspended in a mixture of 20 mL of ethanol and 100 mL of water, and 10 mL of concentrated ammonium hydroxide
  4. additionwas added
  5. filtrationThe solid was collected by vacuum filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized twice from 60 mL of 2-propanol at 4° C.
  9. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-d431a66538c84893b390089c634fefdb
Source dataset
uspto-grants-2001_03
Patent number
US06204267B1

Reaction notes

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