Toluene → 3,4-difluorobenzenecarboximidamide

HRID 1360169Notes

Reaction equation

HRID 1360169 reaction equation
C[Al](C)C.C1(C)C=CC=CC=1.[Cl-].[NH4+:13].[F:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=1[F:23])[C:18]#[N:19]>C(Cl)(Cl)Cl>[F:14][C:15]1[CH:16]=[C:17]([C:18](=[NH:13])[NH2:19])[CH:20]=[CH:21][C:22]=1[F:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 5872033,4-DifluorobenzonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 41827073,4-difluorobenzenecarboximidamideYield 33%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

3.6 mL (7.2 mmol) of trimethyl aluminum (2.0 M toluene solution) was dropwise added to a 10 mL of toluene containing 384 mg (7.17 mmol) of ammonium chloride at room temperature. After stirring for 1.5 hours, 1 g (7.1 mmol) of 3,4-difluorobenzonitrile was added thereto and the resulting mixture was heated to 85° C. for 9 hours. After completion of a reaction, the reaction solution was poured into 100 mL of chloroform containing 200 g of silicagel and filtered off. The residue was washed with 200 mL of methanol and distillation was conducted to give 370 mg (2.36 mmol) of the title compound in a yield of 33%.

Workup

  1. customAfter completion of a reaction
  2. filtrationfiltered off
  3. washThe residue was washed with 200 mL of methanol and distillation

Sources & evidence

ORD record
ord-af231b99fa5f40a2a3dad2e73fc2767c
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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