Chloroform → HCID 12784283, compound

HRID 1577866Notes

Reaction equation

HRID 1577866 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([N:9]=[C:10]=[S:11])[CH:6]=[CH:7][CH:8]=1.Br.Br[CH2:16][CH2:17][NH2:18].C(=O)([O-])[O-].[Na+].[Na+].C(Cl)(Cl)Cl>O>[F:13][C:2]([F:12])([F:1])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:18]2[CH2:17][CH2:16][S:11][C:10]2=[N:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:12])[F:13])[CH:4]=2)=[S:11])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 1372321-Isothiocyanato-3-(trifluoromethyl)benzeneHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 12784283HCID 12784283, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.1 g. of m-trifluoromethylphenyl isothiocyanate, 6.8 g. of 2-bromoethylamine hydrobromide, 3.5 g. of sodium carbonate, and about 100 ml. of chloroform was stirred at ambient temperature for about 14 hours. To the reaction mixture was added about 50 ml. of water. The aqueous phase was washed with chloroform which was added to the organic phase. The organic phase then was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. After filtering, the solvent was removed under reduced pressure. The residue was recrystallized from petroleum ether to give N-(3-trifluoromethylphenyl)-2-(3-trifluoromethylphenylimino)-3-thiazolidinecarbothioamide, m.p. 116°-7°.

Workup

  1. additionA mixture of 6.1 g
  2. additionTo the reaction mixture was added about 50 ml
  3. washThe aqueous phase was washed with chloroform which
  4. additionwas added to the organic phase
  5. washThe organic phase then was washed with saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtering
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was recrystallized from petroleum ether

Sources & evidence

ORD record
ord-466c7ebde5fe42619ca6724a3572be2f
Source dataset
uspto-grants-1981_09
Patent number
US04289778

Reaction notes

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