Methyl iodide → HCID 21283787, compound

HRID 2232439Notes

Reaction equation

HRID 2232439 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[NH:12][N:11]=1.[CH3:25]I>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]([CH3:25])[N:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:22])[F:23])[N:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21283776HCID 21283776, compound

Product 1

HCID 21283787HCID 21283787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.19 g of sodium hydride is placed in 10 ml of N,N-dimethylformamide. A solution of 2.3 g of 3-(o-fluorophenyl)-5-(o-trifluoromethyl-phenyl)-1H-1,2,4-triazole in 15 ml of N,N-dimethylformamide is allowed to drop in while stirring during 10 minutes. After stirring for a further 45 minutes the solution, which has meanwhile become brown, is treated dropwise with 1.17 g of methyl iodide while cooling with ice. The reaction mixture is stirred for a further one hour and thereafter poured on to ice-water, and the aqueous mixture is extracted three times with ethyl acetate. The combined extracts are washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulphate and evaporated under reduced pressure. In this manner there is obtained a mixture of isomeric N-methyltriazoles which can be separated by chromatography on silica gel. By elution with n-hexane/ethyl acetate (19:1) there is obtained pure 5-(o-fluorophenyl)-1-methyl-3-(o-trifluoromethyl-phenyl)-1H-1,2,4-triazole as a resinous product, 1H-NMR(CDCl3): 3.93 (d, CH3, coupling with F).

Workup

  1. stirringAfter stirring for a further 45 minutes the solution, which
  2. temperaturewhile cooling with ice
  3. stirringThe reaction mixture is stirred for a further one hour
  4. extractionthe aqueous mixture is extracted three times with ethyl acetate
  5. washThe combined extracts are washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulphate
  7. customevaporated under reduced pressure
  8. customIn this manner there is obtained
  9. customcan be separated by chromatography on silica gel
  10. washBy elution with n-hexane/ethyl acetate (19:1) there

Sources & evidence

ORD record
ord-116d741caeeb47dda12d9a67c6295f14
Source dataset
uspto-grants-1988_11
Patent number
US04788210

Reaction notes

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