1,2-Dichloroethane → HCID 178499177, compound

HRID 1012111Notes

Reaction equation

HRID 1012111 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[CH:6][CH:7]=1.[CH3:11][O:12][C:13]([C:15]1[C:19]([NH2:20])=[CH:18][NH:17][N:16]=1)=[O:14].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:11][O:12][C:13]([C:15]1[C:19]([NH:20][C:8](=[O:10])[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)=[CH:18][NH:17][N:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7470P-Toluic AcidHCID 757711-HydroxybenzotriazoleHCID 178499176HCID 178499176, compound

Product 1

HCID 178499177HCID 178499177, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of p-toluic acid (272 mg), 4-amino-1H-pyrazole-3-carboxylic acid methyl ester (310 mg), EDC (460 mg) and HOBt (324 mg) in DMF (8 ml) was stirred at ambient temperature for 48 h. The mixture was reduced in vacuo, partitioned between EtOAc and saturated aqueous NaHCO3 and then the organic portion washed with brine, dried (MgSO4) and reduced in vacuo to give 4-(4-methyl-benzoylamino)-1H-pyrazole-3-carboxylic acid methyl ester (486 mg).

Workup

  1. custompartitioned between EtOAc and saturated aqueous NaHCO3
  2. washthe organic portion washed with brine
  3. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-2c7ca66bdd3f423182c5b67f8a72b753
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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