Water → 4-Nitro-6-(trifluoromethyl)-1,3-benzodithiole-2-thione

HRID 1448661Notes

Reaction equation

HRID 1448661 reaction equation
C([SH-:5][C:6](=[S:24])[SH-:7][C:8]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][C:9]=1[N+]([O-])=O)(C)(C)C.O>C(O)(=O)C>[N+:14]([C:13]1[C:8]2[S:7][C:6](=[S:24])[S:5][C:9]=2[CH:10]=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:12]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 962WaterHCID 178454985HCID 178454985, compound

Product 1

HCID 126377344-Nitro-6-(trifluoromethyl)-1,3-benzodithiole-2-thioneYield 55%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

15 g (0.037 mole) of III was dissolved in 125 ml of glacial acetic acid and heated to 90°-100° C. for 45 minutes. The mixture was poured into 500 ml of water, extracted with three 100 ml portions of methylene chloride. The organic extract was dried (Na2SO4) and solvent removed by distillation in vac. The residual solid was recrystallized from ethanol. There was obtained 6.0 g (55% theor.) of 4-nitro-6-trifluoromethyl-1,3-benzodithiole-2-thione, m.p. 163°-165° C. Analytical: Calcd. for C8H2F3NO2S3 : C, 32.32; H, 0.67; S, 32.32. Found: C, 32.18; H, 0.74; S, 32.21. Mass Spectrum mol. wt.=297. NMR(d6DMSO); 8.63δ(1H,m); 8.73(1H,m).

Workup

  1. temperatureheated to 90°-100° C. for 45 minutes
  2. extractionextracted with three 100 ml portions of methylene chloride
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4) and solvent
  5. customremoved by distillation in vac
  6. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-f9a85d451ba4423d9912b1c40aec386a
Source dataset
uspto-grants-1980_02
Patent number
US04187096

Reaction notes

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