Water → HCID 13914154, compound

HRID 622285Notes

Reaction equation

HRID 622285 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:21])([F:20])[F:19])=[C:13]([Cl:22])[C:12]=2[Cl:23])[N:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25].O>CS(C)=O>[N:1]([C:6]1[N:10]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([C:18]([F:20])([F:21])[F:19])=[C:13]([Cl:22])[C:12]=2[Cl:23])[N:9]=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 13689609HCID 13689609, compound

Product 1

HCID 13914154HCID 13914154, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.0 g (0.015 mol) of sodium azide is added to 3.0 g (0.007 mol) of 5-bromo-4-nitro-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazole in 50 ml of dimethylsulphoxide, the mixture is stirred at room temperature for 15 hours, poured into 150 ml of water and extracted several times with chloroform and ethyl acetate, the combined organic phases are dried over magnesium sulphate and concentrated in vacuo and the oily crude produc is purified by chromatography (silica gel; mobile phase: chloroform/acetone 9:1). 0.68 g (24% of theory) of 5-azido-4-nitro-1-(2,3,6-trichloro-4-trifluoromethyl-phenyl)-pyrazole of melting point 84° C.-88° C. is obtained.

Workup

  1. extractionextracted several times with chloroform and ethyl acetate
  2. dry with materialthe combined organic phases are dried over magnesium sulphate
  3. concentrationconcentrated in vacuo
  4. customthe oily crude produc is purified by chromatography (silica gel; mobile phase: chloroform/acetone 9:1)

Sources & evidence

ORD record
ord-244e117507af4511bb3f1fe8f332184b
Source dataset
uspto-grants-1988_09
Patent number
US04770688

Reaction notes

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