1-Butanol → HCID 178512087, compound

HRID 2419789Notes

Reaction equation

HRID 2419789 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.[C:17]1([C:23]2([CH2:26][NH2:27])[CH2:25][CH2:24]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)CCC>O.C(OCC)(=O)C>[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:27][CH2:26][C:23]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:25][CH2:24]1)=[NH:11]

Participants

6

Reactant 3

HCID 2631-ButanolHCID 702871-PhenylcyclopropanemethanamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 178512087HCID 178512087, compound

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 of 1-phenylcyclopropanemethylamine 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 is 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. 136.5°-138.5° 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-6e61b52471494f1da62702b2cb0f3443
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

Loading…