1-Butanol → 1-{[1-(p-Chlorophenyl)cyclopropyl]methyl}-3-(2,6-dichlorobenzylideneamino)guanidine

HRID 2419790Notes

Reaction equation

HRID 2419790 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.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2([CH2:27][NH2:28])[CH2:26][CH2:25]2)=[CH:20][CH:19]=1.C(O)CCC>O.C(OCC)(=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2([CH2:27][NH:28][C:8]([NH:7][N:6]=[CH:5][C:4]3[C:12]([Cl:16])=[CH:13][CH:14]=[CH:15][C:3]=3[Cl:2])=[NH:11])[CH2:25][CH2:26]2)=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 4120166[1-(4-Chlorophenyl)cyclopropyl]methanamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 1785120881-{[1-(p-Chlorophenyl)cyclopropyl]methyl}-3-(2,6-dichlorobenzylideneamino)guanidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7.80 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide and 4.37 g. of 1-(p-chlorophenyl)cyclopropanemethylamine in 100 ml. of n-butanol and 25 ml. of water is heated at reflux for 24 hours. The solution is cooled, diluted with water to a final volume of 2 liters and allowed to stand. Filtration gives a tan solid which is dissolved in ethyl acetate and purified by silica gel column chromatography. Crystallization of the product from diethyl ether gives the desired final product as colorless crystals, m.p. 126°-128° C.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureThe solution is cooled
  3. filtrationFiltration
  4. customgives a tan solid which
  5. custompurified by silica gel column chromatography
  6. customCrystallization of the product from diethyl ether

Sources & evidence

ORD record
ord-4944ab98b94743809047afb25af45334
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

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