1,2-Dichloroethane → HCID 178521932, compound

HRID 132021Notes

Reaction equation

HRID 132021 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].[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[C:13]1([NH:12][C:9]([C:5]2[C:4]([N+:1]([O-:3])=[O:2])=[CH:8][NH:7][N:6]=2)=[O:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6115AnilineHCID 757711-HydroxybenzotriazoleHCID 178524956HCID 178524956, compound

Product 1

HCID 178521932HCID 178521932, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Nitropyrazole-3-carboxylic acid (2.5 g; 15.9 mmol) was added to a stirred solution of aniline (1.6 ml; 17.5 mmol), EDC (3.7 g; 19.1 mmol), and HOBt (2.6 g; 19.1 mmol) in N,N-dimethylformamide (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 NaHCO3 solution. The resultant solid was collected by filtration, washed with water and diethyl ether then dried under vacuum to give 2.85 g of the title compound (sodium salt) as a yellow/brown solid. (LC/MS: Rt 2.78, [M+H]+232.95).

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue triturated with ethyl acetate/saturated NaHCO3 solution
  3. filtrationThe resultant solid was collected by filtration
  4. washwashed with water and diethyl ether
  5. customthen dried under vacuum

Sources & evidence

ORD record
ord-994127e0576e40a3a01f58f3f3bbdc9f
Source dataset
uspto-grants-2008_06
Patent number
US07385059B2

Reaction notes

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