Hydrochloric Acid → HCID 178479328, compound

HRID 2419794Notes

Reaction equation

HRID 2419794 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.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22][NH2:23].[OH-].[Na+].Cl>C(OCC)C.C(O)C>[ClH:2].[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]([N:23]=[CH:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([C:18]([F:17])([F:27])[F:28])[CH:20]=1)=[NH:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 759623-(Trifluoromethyl)benzylamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 178479328HCID 178479328, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.88 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide (U.S. Pat. No. 3,657,337) and 4.37 g. of m-(trifluoromethyl)benzylamine [F. N. Freidfelder and Y. H. Ng, J. Pharm. Sci., 54, 1204 (1965)] in 270 ml. of absolute ethanol is heated at reflux for 18 hours. The solution is cooled, made basic with 2N NaOH and the solvent is removed under reduced pressure. The yellow residue is triturated with dichloromethane and the triturate is evaporated under reduced pressure to give a yellow oil. A diethyl ether solution of this oil is treated with ethanolic hydrogen chloride. Filtration gives colorless crystals which are recrystallized from ethanol-diethyl ether, giving the desired product as colorless crystals, m.p. 165°-167° C.

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe solution is cooled
  3. customthe solvent is removed under reduced pressure
  4. customThe yellow residue is triturated with dichloromethane
  5. customthe triturate is evaporated under reduced pressure
  6. customto give a yellow oil
  7. filtrationFiltration
  8. customgives colorless crystals which
  9. customare recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-e8f8bc08de034ee8b2fc421ae65b0956
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

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