Ethanol → 1-(2,6-Dichlorobenzylideneamino)-3-(2-pyridylmethyl)guanidine

HRID 262763Notes

Reaction equation

HRID 262763 reaction equation
I.[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:4]=1[CH:5]=[N:6][NH:7][C:8](=[NH:11])SC.[NH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(O)C>O>[Cl:2][C:3]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:4]=1[CH:5]=[N:6][NH:7][C:8]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)=[NH:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 195092-PyridinemethanamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 1785121061-(2,6-Dichlorobenzylideneamino)-3-(2-pyridylmethyl)guanidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.85 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydriodide (U.S. Pat. No. 3,657,337) and 3.24 g. of 2-(aminomethyl)pyridine in 25 ml. of absolute ethanol is heated under reflux for 20 hours and diluted while hot with 75 ml. of water, causing the separation of an oil. On standing, the oil crystallizes and filtration gives 5.00 g. of pale yellow crystals, m.p. 125°-140° C. Recrystallization from aqueous ethanol gives the desired compound as pale yellow crystals, m.p. 159.5°-161° C.

Workup

  1. temperatureunder reflux for 20 hours
  2. additiondiluted while hot with 75 ml
  3. customthe separation of an oil
  4. customthe oil crystallizes
  5. filtrationfiltration
  6. customgives 5.00 g
  7. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-e355e821ec8245679c76df6f123e72ba
Source dataset
uspto-grants-1979_05
Patent number
US04154947

Reaction notes

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