Dimethylformamide → HCID 23024741, compound

HRID 350123Notes

Reaction equation

HRID 350123 reaction equation
Cl[CH2:2][C:3]1[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])=[CH:5][CH:4]=1.[CH:23]([C:26]1[C:30]([C:31]([O:33]CC)=[O:32])=[CH:29][NH:28][N:27]=1)([CH3:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:23]([C:26]1[C:30]([C:31]([OH:33])=[O:32])=[CH:29][N:28]([CH2:2][C:3]2[CH:22]=[CH:21][C:6]([O:7][CH2:8][C:9]3[N:10]=[C:11]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:12][C:13]=3[CH3:14])=[CH:5][CH:4]=2)[N:27]=1)([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 109469404-(4-Chloromethylphenoxy)methyl-5-methyl-2-phenyloxazoleHCID 178469918HCID 178469918, compound

Product 1

HCID 23024741HCID 23024741, compoundYield 116.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-chloromethylphenoxy)methyl-5-methyl-2-phenyloxazole (7.13 g), ethyl 3-isopropyl-1H-pyrazol-4-carboxylate (6.17 g), potassium carbonate (4.72 g) and N,N-dimethylformamide (70 ml) was stirred at 80° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. A mixture of the residue, potassium hydroxide (4.83 g) and ethanol (150 ml) was refluxed for 5 hours. After the reaction solvent was removed under reduced pressure, water was added to the mixture, then the mixture was acidified with dilute hydrochloric acid. The crystals obtained were collected by filtration to yield 3-isopropyl-1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-carboxylic acid (11.39 g, yield: 78%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 194–195° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionA mixture of the residue, potassium hydroxide (4.83 g) and ethanol (150 ml)
  6. temperaturewas refluxed for 5 hours
  7. customAfter the reaction solvent was removed under reduced pressure, water
  8. additionwas added to the mixture
  9. customThe crystals obtained
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f2193fc2f63d4063b9b74da31ad4c1f9
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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