1-Butanol → HCID 178512118, compound

HRID 2419793Notes

Reaction equation

HRID 2419793 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]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:19]=1[CH2:20][NH2:21].C(O)CCC>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:21][CH2:20][C:19]1[C:18]([F:17])=[CH:25][CH:24]=[CH:23][C:22]=1[F:26])=[NH:11]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 1235632,6-DifluorobenzylamineHCID 178504060Methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide

Product 1

HCID 178512118HCID 178512118, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7.80 g. of methyl 3-(2,6-dichlorobenzylidene)thiocarbazimidate hydroiodide (U.S. Pat. No. 3,657,337) and 2.86 g. of 2,6-difluorobenzylamine (prepared from 2,6-difluorobenzylamine hydrochloride) in 100 ml. of n-butanol and 20 ml. of water is heated at reflux for 66 hours. The solvent is removed under reduced pressure and the residual yellow oil is dissolved in aqueous ethanol and made basic with 10N NaOH. The resultant mixture is extracted with chloroform and the chloroform extract is evaporated under reduced pressure to give a yellow gum. This gum in ethyl acetate is purified by silica gel column chromatography, giving a colorless solid. This solid is recrystallized from aqueous ethanol, giving the desired product as colorless crystals, m.p. 168.5°-169.5° C.

Workup

  1. temperatureat reflux for 66 hours
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residual yellow oil is dissolved in aqueous ethanol
  4. extractionThe resultant mixture is extracted with chloroform
  5. extractionthe chloroform extract
  6. customis evaporated under reduced pressure
  7. customto give a yellow gum
  8. customThis gum in ethyl acetate is purified by silica gel column chromatography
  9. customgiving a colorless solid
  10. customThis solid is recrystallized from aqueous ethanol

Sources & evidence

ORD record
ord-ccd268bb50824b819f3056a7fae6c6cf
Source dataset
uspto-grants-1978_08
Patent number
US04107326

Reaction notes

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