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

HRID 1873465Notes

Reaction equation

HRID 1873465 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:14](=[S:21])[NH:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:2].[CH3:22]C([O-])(C)C.[K+].CI.O>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([C:14]([S:21][CH3:22])=[N:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[N:12][CH:11]=[N:10]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 580920773-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbothioamide

Product 1

HCID 66820051methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioateYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzene-carbothioamide (1.5 g) in THF was added t-BuOK (0.64 g) under cooling (0° C.). After stirring for 15 minutes, methyl iodide (0.81 g) was added dropwise to the mixture under cooling (0° C.). The reaction liquor was returned to room temperature and stirred for 2 hours. Water was added to the reaction mixture, and aqueous layer was extracted with ethyl acetate. The combined organic layer was 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 methyl 3-cyano-4-(1H-1,2,4-triazol-1-yl)-N-[(trimethylsilyl)methyl]benzenecarbimidothioate at a yield of 64%.

Workup

  1. temperatureunder cooling (0° C.)
  2. customwas returned to room temperature
  3. stirringstirred for 2 hours
  4. extractionwas extracted with ethyl acetate
  5. washThe combined organic layer was 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-532613f27bc54dc5a1cf6303070dd43f
Source dataset
uspto-grants-2012_11
Patent number
US08304371B2

Reaction notes

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