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

HRID 262768Notes

Reaction equation

HRID 262768 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[S:20][CH:21]=[CH:22][CH:23]=1.C(O)C>O.[OH-].[Na+]>[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[S:20][CH:21]=[CH:22][CH:23]=1)=[NH:11]

Participants

6

Reactant 3

HCID 702EthanolHCID 34005(2-Thienylmethyl)amineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 1785121161-(2,6-Dichlorobenzylideneamino)-3-(2-thenyl)guanidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5.85 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydriodide and 3.39 g. of 2-(aminomethyl)thiophene in 25 ml. of absolute ethanol is heated under reflux for 16 hours, diluted with water and excess 10N sodium hydroxide is added. After standing, crystallization occurs, and filtration gives 3.50 g. of nearly colorless crystals. Recrystallization from aqueous ethanol gives the desired product as colorless crystals, m.p. 135°-137° C.

Workup

  1. temperatureunder reflux for 16 hours
  2. additionis added
  3. customcrystallization
  4. filtrationfiltration
  5. customgives 3.50 g
  6. customRecrystallization from aqueous ethanol

Sources & evidence

ORD record
ord-99cc69d1626a41b6ac9ae6c77d9a89d0
Source dataset
uspto-grants-1979_05
Patent number
US04154947

Reaction notes

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