Toluene → 4-Fluorobenzamidine

HRID 1360168Notes

Reaction equation

HRID 1360168 reaction equation
C[Al](C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+:13].[F:14][C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[F:14][C:15]1[CH:22]=[CH:21][C:18]([C:19](=[NH:13])[NH2:20])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 145174-FluorobenzonitrileHCID 25517Ammonium ChlorideHCID 16682925Trimethylaluminum

Product 1

HCID 42952384-FluorobenzamidineYield 71%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

4.12 mL (8.24 mmol) of trimethyl aluminum (2.0 M toluene solution) was dropwise added to a 10 mL of toluene containing 441 mg (8.24 mmol) of ammonium chloride at room temperature. After stirring for 1.5 hours, 1 g (8.25 mmol) of 4-fluorobenzonitrile was added thereto and the resulting mixture was heated to 85° C. for 9 hours. After completion of a reaction, the reaction solution was cooled, then poured into 100 mL of chloroform containing 500 g of silica gel and filtered off. The residue was washed with 100 mL of methanol and distillation was conducted to give 821 mg (5.9 mmol) of the title compound in a yield of 71%.

Workup

  1. customAfter completion of a reaction
  2. temperaturethe reaction solution was cooled
  3. filtrationfiltered off
  4. washThe residue was washed with 100 mL of methanol and distillation

Sources & evidence

ORD record
ord-98a2bd389015498a9d65df3fb0cf99e0
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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