Dimethylformamide → HCID 22905793, compound

HRID 1488510Notes

Reaction equation

HRID 1488510 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]2[CH:14]=[N:13][N:12]=[CH:11]2)=[CH:5][CH:4]=1.[H-].[Na+].F[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1.[CH3:29]N(C)C=O>>[N+:26]([C:23]1[CH:24]=[CH:25][C:20]([CH2:29][N:9]([N:10]2[CH:11]=[N:12][N:13]=[CH:14]2)[C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=2)=[CH:21][CH:22]=1)([O-:28])=[O:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 22905775HCID 22905775, compound

Product 1

HCID 22905793HCID 22905793, compound

Procedure

0.23 Gram of 4-[(4-trifluoromethylphenyl)-amino]-4H-1,2,4-triazole was added little by little to an N,N-dimethylformamide suspension of 0.04 g of sodium hydride at room temperature. The mixture was stirred for 30 minutes at room temperature, and 0.15 g of 4-fluoronitrobenzene was added thereto and the mixture was stirred for 15 minutes at 100° C. The solvent was removed by distillation under reduced pressure and water was added to the residue, which was then extracted with chloroform. The chloroform layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. The crystals thus obtained were recrystallized from a mixed solvent of ethyl acetate/ether to give 280 mg of 4-[N-(4-nitrobenzyl)-N-(4-trifluoromethylphenyl)amino]-4H-1,2,4-triazole.

Workup

  1. stirringthe mixture was stirred for 15 minutes at 100° C
  2. customThe solvent was removed by distillation under reduced pressure and water
  3. additionwas added to the residue, which
  4. extractionwas then extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation
  8. customThe crystals thus obtained
  9. customwere recrystallized from a mixed solvent of ethyl acetate/ether

Sources & evidence

ORD record
ord-6f81e32301bf42aab70be3f7c43e31b7
Source dataset
uspto-grants-1997_10
Patent number
US05674886

Reaction notes

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