Dimethylformamide → 1-Methylbenzotriazole

HRID 2166057Notes

Reaction equation

HRID 2166057 reaction equation
N1C=NC=N1.CN(C)C=O.[H-].[Na+].ClC(C1C=CC(Cl)=CC=1)[C:15]1[CH:16]=[CH:17][C:18]2[N:22]=[N:21][N:20]([CH3:23])[C:19]=2[CH:24]=1>O>[CH3:23][N:20]1[C:19]2[CH:24]=[CH:15][CH:16]=[CH:17][C:18]=2[N:22]=[N:21]1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 149906726-[chloro(4-chlorophenyl)methyl]-1-methyl-1H-benzotriazole

Product 1

HCID 259021-Methylbenzotriazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 28.4 parts of 1H-1,2,4-triazole in 135 parts of N,N-dimethylformamide were added 11.4 parts of a sodium hydride dispersion 80% under nitrogen atmosphere. After stirring for 1 hour at room temperature, a solution of 40 parts of 6-[chloro(4-chlorophenyl)-methyl]-1-methyl-1H-benzotriazole in 90 parts of N,N-dimethylformamide was added to the mixture. The whole was stirred for 1 hour at 60° C. The reaction mixture was diluted with 50 parts of water and the whole was evaporated. The residue was extracted with ethyl acetate. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane. The product was filtered off and dried, yielding 13 parts (29.2%) of 6-[(4-chlorophenyl)-1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole; mp. 178.9° C. (compound 64).

Workup

  1. stirringThe whole was stirred for 1 hour at 60° C
  2. customthe whole was evaporated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (99:1 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from a mixture of 2-propanone and 1,1'-oxybisethane
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-921c8d579d6b49ed9c42083c970d3752
Source dataset
uspto-grants-1990_07
Patent number
US04943574

Reaction notes

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