Toluene → 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbothioamide

HRID 1873464Notes

Reaction equation

HRID 1873464 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)[C:6]([NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=O)#[N:2].C1(C)C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:38])=CC=1>O>[C:1]([C:3]1[CH:4]=[C:5]([C:6](=[S:38])[NH:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[N:20][CH:19]=[N:18]1)#[N:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 580920883-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzamide

Product 1

HCID 580920773-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbothioamideYield 129.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzamide (1.1 g) was dissolved with toluene. To the mixture was added Lawesson reagent (1.5 g) and heated to reflux for 5 hours. The reaction mixture was returned to room temperature, water was added thereto, and the aqueous layer was extracted with ethyl acetate. The combined organic layers, were washed with a saturated aqueous sodium hydrogen carbonate solution, subsequently dried over magnesium sulfate. After filtering the reaction mixture, the solvent was distilled off under reduced pressure, and the resulting mixture was purified by silica gel chromatography, to obtain 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbothioamide (1.5 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. customwas returned to room temperature
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers, were washed with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialsubsequently dried over magnesium sulfate
  7. filtrationAfter filtering the reaction mixture
  8. distillationthe solvent was distilled off under reduced pressure
  9. customthe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-390993d722a04689a663c0a92e90f832
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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