Diethyl Ether → HCID 19778369, compound

HRID 1031149Notes

Reaction equation

HRID 1031149 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([Cl:33])[C:24]=1[N:34]1[N:38]=[C:37]([CH2:39][OH:40])[C:36]([CH3:41])=[N:35]1.CCOCC>ClCCl>[Cl:33][C:25]1[CH:26]=[C:27]([C:29]([F:32])([F:30])[F:31])[CH:28]=[C:23]([Cl:22])[C:24]=1[N:34]1[N:38]=[C:37]([CH:39]=[O:40])[C:36]([CH3:41])=[N:35]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 2724130Cornforth reagentHCID 19778391HCID 19778391, compound

Product 1

HCID 19778369HCID 19778369, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium dichromate (7.5 g) was added, with stirring, to a solution of crude [2-(2,6-dichloro-4-trifluoromethylphenyl)-5-methyl-2H-1,2,3-triazol-4-yl]methanol (4.3 g) in dichloromethane (50 ml) at room temperature. The mixture was stirred overnight and then ether (100 ml) and silica (4 g) was added. After 10 minutes, the mixture was filtered through a pad of magnesium sulphate and the solvent was evaporated to give 2-(2,6-dichloro-4-trifluoromethylphenyl]-5-methyl-2H-1,2,3-triazole-4-carboxaldehyde, as a crude brown solid. This product was then treated in similar manner to Example 1 with diaminomaleonitrile to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylimino))methyl]-5-methyl-2H-1,2,3-triazole, m.p. 238°-239°.

Workup

  1. waitAfter 10 minutes
  2. filtrationthe mixture was filtered through a pad of magnesium sulphate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-301abf77485046abb4fce8c77becfe39
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Reaction notes

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