Dimethylformamide → HCID 23402488, compound

HRID 1063797Notes

Reaction equation

HRID 1063797 reaction equation
C(Cl)(=O)C(Cl)=O.[CH2:7]([C:11]1[NH:15][N:14]=[C:13]([C:16](O)=[O:17])[C:12]=1[N+:19]([O-:21])=[O:20])[CH2:8][CH2:9][CH3:10].C[N:23](C)C=O>ClCCl>[CH2:7]([C:11]1[NH:15][N:14]=[C:13]([C:16]([NH2:23])=[O:17])[C:12]=1[N+:19]([O-:21])=[O:20])[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 22277496HCID 22277496, compound

Product 1

HCID 23402488HCID 23402488, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Oxalyl chloride (12.3 ml, 141 mmol) was added dropwise to a suspension of 5-butyl-4-nitro-1H-pyrazol-3-carboxylic acid (10 g, 46.9 mmol) in dichloromethane (100 ml) containing dimethylformamide (0.5 ml) under nitrogen at 0° C. The reaction was stirred at 0° C. for 1 hours, allowed to warm to room temperature and stirred for a further 2 hours. The solvent was removed under reduced pressure, the residue was dissolved in toluene (100 ml) and ammonia gas was bubbled into the solution for 2 hours. The reaction was stirred under nitrogen at room temperature for 18 hours, concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (9:1, by volume) to give 5-butyl-4-nitro-1H-pyrazol-3-carboxylic acid amide (3.1 g) as an orange solid. 1H NMR (400 MHz, DMSO-D6): δ=7.87-7.96 (1H, brs), 7.57-7.66 (1H, brs), 2.83-2.90 (2H, t), 1.56-163 (2H, quin), 1.24-1.36 (2H, sext), 0.84-0.92 (3H, t) ppm. LRMS (electrospray): m/z [M−H]+ 211. Anal. Found C, 44.66; H, 5.56; N, 25.50. C8H12N4O3.0.23 mol H2O requires C, 44.41; H, 580; N, 25.90%.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a further 2 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in toluene (100 ml)
  5. customammonia gas was bubbled into the solution for 2 hours
  6. stirringThe reaction was stirred under nitrogen at room temperature for 18 hours
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol (9:1, by volume)

Sources & evidence

ORD record
ord-9f38d1d2544e489f9fbbb2a314e4390e
Source dataset
uspto-grants-2005_11
Patent number
US06967204B2

Reaction notes

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