Ethanol → 4-Methylbenzene-1-carboximidamide hydrochloride

HRID 651392Notes

Reaction equation

HRID 651392 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](=[NH:9])O)=[CH:5][CH:4]=1.[NH3:12].CO.[Cl-].[NH4+].CCO>CO>[ClH:1].[CH3:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:12])=[NH:9])=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 21705897Ammonia methanolHCID 178425648HCID 178425648, compound2×

Product 1

HCID 1227534-Methylbenzene-1-carboximidamide hydrochlorideYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of p-methylbenzimidate hydrochloride (8.00 g, 43.09 mmol) in MeOH (100 ml) is added NH3/MeOH solution (2.68M, 24.12 ml, 64.64 mmol). Upon the addition of the NH3, the mixture has a pH around 8.5. To this solution is added ammonium chloride (2.30 g, 43.09 mmol). The reaction mixture is stirred at room temperature for 20 hours, then cooled in refrigerator and the precipitate is remoiva by filtration. The mother liquor is concentrated to yield the crude product which is taken up in a limited amount of cold EtOH and the white precipitate is filtered. The beige filtrate is concentrated to yield p-methylbenzamidine hydrochloride as an off-white solid (7.15 g, 97%). 1H NMR (DMSOd6): δ 2.41 (s, 3H), 7.43 (d, 2H), 7.78 (d, 2H), 9.24-9.39 (broad d, 3H).

Workup

  1. temperaturecooled in refrigerator
  2. filtrationby filtration
  3. concentrationThe mother liquor is concentrated
  4. customto yield the crude product which
  5. filtrationthe white precipitate is filtered
  6. concentrationThe beige filtrate is concentrated

Sources & evidence

ORD record
ord-58e2f46f35824b79ae80771dc162f57b
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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