1,2-Dichloroethane → HCID 178522146, compound

HRID 1624931Notes

Reaction equation

HRID 1624931 reaction equation
[N+:1]([C:4]1[C:5]([C:9]([OH:11])=O)=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:9]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=2)=[O:11])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 178524956HCID 178524956, compound

Product 1

HCID 178522146HCID 178522146, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitropyrazole-3-carboxylic acid (10 g; 63.66 mmol) was added to a stirred solution of 4-fluoroaniline (6.7 ml; 70 mmol), EDC (14.6 g; 76.4 mmol), and HOBt (10.3 g; 76.4 mmol) in DMF (25 ml), then stirred at room temperature overnight. The solvent was removed by evaporation under reduced pressure and the residue triturated with ethyl acetate/saturated brine solution. The resultant yellow solid was collected by filtration, washed with 2M hydrochloric acid, then dried under vacuum to give 15.5 g of the title compound. (LC/MS: Rt 2.92 [M+H]+ 250.89).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue triturated with ethyl acetate/saturated brine solution
  3. filtrationThe resultant yellow solid was collected by filtration
  4. washwashed with 2M hydrochloric acid
  5. customdried under vacuum

Sources & evidence

ORD record
ord-9ddc8d1a08d441d39c40020df0e6b260
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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