Methanol → HCID 58326407, compound

HRID 1666191Notes

Reaction equation

HRID 1666191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([OH:23])=[O:22])[CH2:9]2)=[CH:4][CH:3]=1.CO.[CH3:26]C1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:26][O:22][C:21]([C:10]1[CH2:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[N:11]=1)=[O:23]

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 11773086HCID 11773086, compound

Product 1

HCID 58326407HCID 58326407, compoundYield 498.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (78.0 g, 0.21 mol), methanol 150 mL, p-TsOH.H2O (0.042 mol) in toluene (350 mL) was stirred for 24 hours at 80° C. The reaction mixture was cooled to room temperature and the solvent was concentrated in vacuo. The residue was taken up in EtOAc (300 mL) and subsequently washed with sat. aq. NH4Cl and water and dried. The solvent was removed in vacuo to yield the title compound (80.27 g, 99%) white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationthe solvent was concentrated in vacuo
  3. washsubsequently washed with sat. aq. NH4Cl and water
  4. customdried
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-90a23f7868354de8939ed007c3522cf3
Source dataset
uspto-grants-2011_10
Patent number
US08044053B2

Reaction notes

Loading…