Cyanamide → HCID 178427233, compound

HRID 1263001Notes

Reaction equation

HRID 1263001 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[CH3:12].[N:13]#[C:14][NH2:15]>C(O)C>[ClH:1].[NH:2]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[CH3:12])[C:14]([NH2:15])=[NH:13]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 70061652HCID 70061652, compound

Product 1

HCID 178427233HCID 178427233, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To 140 ml of ethanol, was added 22.6 g of 4-amino-3-methylbenzoic acid hydrochloride followed by 7.6 g of cyanamide. After having been stirred overnight at 60° C., the reaction mixture was freed from the solvent by distillation under reduced pressure and mixed with acetone to collect the crystals by filtration. The crystals were washed with acetone and recrystallized from a mixture of ethanol and ethyl acetate to obtain 8.9 g of white granular crystals of 4-guanidino-3-methylbenzoic acid hydrochloride.

Workup

  1. distillationthe reaction mixture was freed from the solvent by distillation under reduced pressure
  2. additionmixed with acetone
  3. customto collect the crystals
  4. filtrationby filtration
  5. washThe crystals were washed with acetone
  6. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-c8249cb80b3140d3a1e7044a0626d3a9
Source dataset
uspto-grants-1984_06
Patent number
US04454338

Reaction notes

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