Chloroform → 2-Ethoxybenzamidine hydrochloride

HRID 1016347Notes

Reaction equation

HRID 1016347 reaction equation
[Cl-].[NH4+:2].C[Al](C)C.[CH2:7]([O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13])[CH3:8].C(Cl)(Cl)[Cl:19]>C1(C)C=CC=CC=1.CCCCCC>[ClH:19].[CH2:7]([O:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]([NH2:2])=[NH:13])[CH3:8]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 5769222-EthoxybenzonitrileHCID 16682925Trimethylaluminum

Product 1

HCID 123012442-Ethoxybenzamidine hydrochloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

21.4 g (400 mmol) of ammonium chloride are suspended in 375 ml of toluene, and the suspension is cooled to 0° C. 200 ml of a 2M solution of trimethylaluminium in hexane are added dropwise, and the mixture is stirred at room temperature until evolution of gas has ceased. 29.44 g (200 mmol) of 2-ethoxybenzonitrile are added, and the reaction mixture is then stirred at 80° C. (bath) overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 100 g of silica gel and 950 ml of chloroform, and the mixture is stirred at room temperature for 30 minutes. The mixture is filtered off with suction and the filter residue is washed with the same amount of methanol. The mother liquor is evaporated, the resulting residue is stirred with a mixture of dichloromethane and methanol (9:1), the solid is filtered off with suction and the mother liquor is evaporated. This gives 30.4 g (76%) of a colourless solid.

Workup

  1. stirringthe reaction mixture is then stirred at 80° C. (bath) overnight
  2. customThe cooled reaction mixture
  3. temperaturecooling
  4. stirringthe mixture is stirred at room temperature for 30 minutes
  5. filtrationThe mixture is filtered off with suction
  6. washthe filter residue is washed with the same amount of methanol
  7. customThe mother liquor is evaporated
  8. stirringthe resulting residue is stirred with a mixture of dichloromethane and methanol (9:1)
  9. filtrationthe solid is filtered off with suction
  10. customthe mother liquor is evaporated

Sources & evidence

ORD record
ord-5a433b30e2894f3d8e76a1c1cdd81bb1
Source dataset
uspto-grants-2002_11
Patent number
US06476029B1

Reaction notes

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