Ammonium Chloride → HCID 178422378, compound

HRID 254825Notes

Reaction equation

HRID 254825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]#[N:22])[C:9]=2[CH3:23])=[CH:4][CH:3]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]3[NH:26][N:25]=[N:24][N:22]=3)[C:9]=2[CH3:23])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 668444145-(4-chloro phenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile

Product 1

HCID 178422378HCID 178422378, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonitrile (500 mg, 1.39 mmol), sodium azide (1.08 g, 16.6 mmol) and ammonium chloride (890 mg, 16.6 mmol) dissolved in dimethylformamide (3 ml) was placed in a microwave synthesizer tube, and subjected to microwave irradiation in a Biotage® Initiator was set at 180° C. After 20 minutes, the mixture was quenched with water and extracted with ethyl acetate. The solvent of the extracted organic layer was evaporated off and the residue was purified by reverse phase preparative HPLC, to obtain 5-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-1H-tetrazole (550 mg, 98%) as white solid.

Workup

  1. customwas placed in a microwave synthesizer tube
  2. customirradiation in a Biotage® Initiator
  3. customwas set at 180° C
  4. customthe mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe solvent of the extracted organic layer was evaporated off
  7. customthe residue was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-6e4bc0111f2043f3bd74e405d8761d50
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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