Hydrochloric Acid → 5-Azido-4-cyano-1-(2,4-dichlorophenyl)-pyrazole

HRID 622286Notes

Reaction equation

HRID 622286 reaction equation
CCOCC.[N:6]([O-])=O.[Na+].[NH:10]([C:12]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:15]=[CH:14][C:13]=1[C:25]#[N:26])[NH2:11].Cl>O>[N:10]([C:12]1[N:16]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])[N:15]=[CH:14][C:13]=1[C:25]#[N:26])=[N+:11]=[N-:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl Ether2×HCID 137557984-Cyano-5-hydrazino-1-(2,4-dichlorophenyl)-pyrazoleHCID 23668193Sodium Nitrite

Product 1

HCID 139141555-Azido-4-cyano-1-(2,4-dichlorophenyl)-pyrazoleYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

10 ml of ether and then 0.85 g (0.012 mol) of sodium nitrite in 10 ml of water are added to 2.7 g (0.01 mol) of 5-hydrazino-4-cyano-1-(2,4-dichlorophenyl)-pyrazole in a solution of 1.9 ml of concentrated hydrochloric acid in 10 ml of water at 0° C. When the addition has ended, a further 20 ml of water and 30 ml of ether are added, the mixture is filtered, the ether phase is separated off, dried over calcium chloride and concentrated in vacuo and the oil thus obtainable is purified by chromatography (silica gel; mobile phase: methylene chloride/acetone 9:1). 1.2 g (43% of theory) of 5-azido-4-cyano-1-(2,4-dichlorophenyl)-pyrazole are obtained as an oil.

Workup

  1. additionWhen the addition
  2. filtrationthe mixture is filtered
  3. customthe ether phase is separated off
  4. dry with materialdried over calcium chloride
  5. concentrationconcentrated in vacuo
  6. customthe oil thus obtainable is purified by chromatography (silica gel; mobile phase: methylene chloride/acetone 9:1)

Sources & evidence

ORD record
ord-6ce9b6be877742b2827af283c5886e65
Source dataset
uspto-grants-1988_09
Patent number
US04770688

Reaction notes

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