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

HRID 262764Notes

Reaction equation

HRID 262764 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:20]=[N:21][CH:22]=[CH:23][CH:24]=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:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[NH:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 310183-PyridinemethanamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 1785121111-(2,6-Dichlorobenzylideneamino)-3-(3-pyridylmethyl)guanidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.85 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydriodide, 3.24 g. of 3-(aminomethyl)pyridine and 25 ml. of absolute ethanol is heated under reflux for 24 hours and diluted while hot with 75 ml. of water. After cooling, an oil separates and crystallizes. The mixture is chilled overnight and the crystals are separated and recrystallized from 100 ml. of 50% aqueous ethanol to give the desired product as pale yellow crystals, m.p. 148°-151° C.

Workup

  1. additionA mixture of 5.85 g
  2. temperatureunder reflux for 24 hours
  3. additiondiluted while hot with 75 ml
  4. temperatureAfter cooling
  5. customan oil separates and crystallizes
  6. temperatureThe mixture is chilled overnight
  7. customthe crystals are separated
  8. customrecrystallized from 100 ml

Sources & evidence

ORD record
ord-8c8de0a855b04af48e24d7a007cf8f02
Source dataset
uspto-grants-1979_05
Patent number
US04154947

Reaction notes

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