Phosphorus oxychloride → HCID 178510233, compound

HRID 1801889Notes

Reaction equation

HRID 1801889 reaction equation
[N+:1]([C:4]1[CH:8]=[C:7]([C:9]([NH2:11])=O)[NH:6][N:5]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[N+:1]([C:4]1[CH:8]=[C:7]([C:9]#[N:11])[NH:6][N:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178513690HCID 178513690, compound

Product 1

HCID 178510233HCID 178510233, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-nitro-1H-pyrazole-5-carboxamide (3.0 g, 19.2 mmol) in pyridine (30 mL) was treated with phosphorus oxychloride (5.9 g) and the resultant solution was stirred for 3 h at rt. The reaction mixture was diluted with ice, then extracted with DCM (100 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the crude 3-nitro-1H-pyrazole-5-carbonitrile, which was used directly in the next step without further purification. LC-MS (ESI) m/z 137 (M−H)−.

Workup

  1. additionThe reaction mixture was diluted with ice
  2. extractionextracted with DCM (100 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2eda9be2f22b47a6bb8582bad973b018
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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