Ammonia → 3,5-Dimethoxy-benzamidine

HRID 1793887Notes

Reaction equation

HRID 1793887 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1)[C:6]#[N:7].[NH3:13]>C(O)C.CO>[CH3:12][O:11][C:9]1[CH:8]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:10]=1)[C:6]([NH2:13])=[NH:7]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 294821-(Cyanomethyl)-3,5-dimethoxybenzene

Product 1

HCID 36278493,5-Dimethoxy-benzamidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Dry HCl gas was bubbled through a cooled (−15° C.) solution of 3,5-dimethoxybenzonitrile (1.50 g, 9.20 mmol) for 30 minutes. The reaction mixture was placed in a refrigerator overnight. After evaporation of the solvent, a white solid was obtained which was dissolved in ethanol. 9.2 ml of a 2 molar solution of ammonia in Methanol was added and the reaction mixture was stirred at room temperature overnight. After evaporation of the solvent, the title compound, MS: m/e=181.2 (M+H+), (1.21 g, 71%) was obtained by chromatographic purification of the residue (silica gel, MeOH, DCM). 1H-NMR (300 MHz, d6-DMSO, 25° C.): δ(ppm)=3.80 (6H, s), 6.82 (1H, t, J=2 Hz), 7.05 (2H, t, J=2 Hz), 9.35 (3H, bs).

Workup

  1. customDry HCl gas was bubbled through
  2. customwas placed in a refrigerator overnight
  3. customAfter evaporation of the solvent
  4. customa white solid was obtained which
  5. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-312075c6fd5a4ebca61e82b4b8c1015b
Source dataset
uspto-grants-2006_04
Patent number
US07022718B2

Reaction notes

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