1,2-Dichloroethane → 4-bromo-1,3-dimethyl-1H-pyrazole-5-carboxamide

HRID 58061

Reaction equation

HRID 58061 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[N:4][N:5]([CH3:10])[C:6]=1[C:7](O)=[O:8].[Cl-].[NH4+].C1C=CC2N(O)N=[N:20]C=2C=1.C(Cl)CCl.C(N(C(C)C)C(C)C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:11])=[N:4][N:5]([CH3:10])[C:6]=1[C:7]([NH2:20])=[O:8]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27798334-bromo-1,3-dimethyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 47661424-bromo-1,3-dimethyl-1H-pyrazole-5-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-bromo-1,3-dimethyl-1H-pyrazole-5-carboxylic acid (0.3 g, 1.370 mmol) in DMF (5 mL) were added ammonium chloride (0.293 g, 5.48 mmol), HOBt (0.222 g, 1.644 mmol), and EDC (0.368 g, 1.917 mmol), followed by N-ethyl-N-isopropylpropan-2-amine (1.193 mL, 6.85 mmol). The reaction mixture was stirred for 18 hours at room temperature. The reaction mixture was subsequently diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated to give the title compound, which was used without further purification (0.28 g).

Workup

  1. washwashed with brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cc234f99af78493bbb90bc9a27ab3330
Source dataset
uspto-grants-2016_09
Patent number
US09434743B2

Linked notes

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