Ammonia → HCID 178513690, compound

HRID 1801888Notes

Reaction equation

HRID 1801888 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1)([O-:3])=[O:2].C(N1C=CN=C1)([N:14]1C=CN=C1)=O.N>CN(C=O)C.CO>[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([NH2:14])=[O:11])[NH:7][N:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 178513690HCID 178513690, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-nitro-3-pyrazolecarboxylic acid (6.28 mg, 40 mmol) in DMF (30 mL) was added carbonyldiimidazole (12.96 mg, 80 mmol) The mixture was allowed to stir for 30 min, and ammonia in MeOH (2M, 60 mL) was added. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure to afford the crude product which was then washed with ether to afford 3-nitro-1H-pyrazole-5-carboxamide (3.0 g, 48%), which was used directly in the next step without further purification. LC-MS (ESI) m/z 155 (M−H)−.

Workup

  1. stirringThe reaction mixture was stirred at rt overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customto afford the crude product which
  4. washwas then washed with ether

Sources & evidence

ORD record
ord-9cf9467032654afe8732eaf5721920b5
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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