Dimethyl Sulfoxide → HCID 22244651, compound

HRID 891152Notes

Reaction equation

HRID 891152 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:5]([CH3:13])[NH:4][N:3]=1.Cl[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:13][C:5]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:2]([CH3:1])[N:3]([C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][N:16]=2)[N:4]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 2753118HCID 2753118, compoundHCID 2799611Ethyl 6-chloronicotinate

Product 1

HCID 22244651HCID 22244651, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 3,5-dimethyl-4-phenyl-1H-pyrazole (2.50 g, 14.5 mmol), ethyl 6-chloronicotinate (5.39 g, 29.0 mmol), potassium carbonate (8.02 g, 58.1 mmol) and dimethyl sulfoxide (100 mL) was stirred at 160° C. for 16 h. After cooling to room temperature, the mixture was diluted with ethyl acetate and toluene (2:1) and washed with water. The organic fraction was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with hexane/ethyl acetate (8:1) to afford 2.43 g (52%) of the title compound: MS (ESI) m/z 322 [M+H]+, 1H-NMR (CDCl3) δ 9.06-9.05 (1H, m), 8.39-8.36 (1H, m), 8.04-8.01 (1H, m), 7.48-7.29 (5H, m), 4.42 (2H, q, J=7.2 Hz), 2.67 (3H, s), 2.32 (3H, s), 1.43 (3H, t, J=7.2 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe organic fraction was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica-gel column chromatography
  6. washeluting with hexane/ethyl acetate (8:1)

Sources & evidence

ORD record
ord-9b2a28fb37d942f2a08b1aeeeff3606d
Source dataset
uspto-grants-2006_02
Patent number
US07001917B2

Reaction notes

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