Dimethylformamide → HCID 178463133, compound

HRID 1661962

Reaction equation

HRID 1661962 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([OH:11])=O.C(Cl)(=O)C(Cl)=O.CN(C=O)C.Cl.[OH:32][C:33]1[N:37]([CH2:38][CH3:39])[N:36]=[CH:35][CH:34]=1>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([C:9]([C:34]2[CH:35]=[N:36][N:37]([CH2:38][CH3:39])[C:33]=2[OH:32])=[O:11])[CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 667565243-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acidHCID 178463041HCID 178463041, compound

Product 1

HCID 178463133HCID 178463133, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (200 mg, 6.90×10−4 mol) in chloroform (15 mL) were added oxalyl chloride (0.5 mL) and DMF in a catalytic amount. The reaction mixture was stirred at room temperature for 30 minutes, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-ethylpyrazole hydrochloride (134 mg, 9.01×10−4 mol), triethylamine (139 mg) and N,N-dimethylaminopyridine (170 mg) were added. The mixture was heated at refluxed temperature for 1 hour. The reaction mixture was allowed to cool to room temperature, and then ethyl acetate (200 mL) was added. The mixture was washed twice with a saturated brine, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (139 mg) and acetone cyanohydrin in a catalytic amount were added, followed by stirring for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-ethylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. dissolutionThe residue was dissolved in anhydrous THF (20 mL)
  3. temperatureThe mixture was heated
  4. temperatureat refluxed temperature for 1 hour
  5. temperatureto cool to room temperature
  6. washThe mixture was washed twice with a saturated brine
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. dissolutionThe residue was dissolved in anhydrous acetonitrile (10 mL)
  10. additiontriethylamine (139 mg) and acetone cyanohydrin in a catalytic amount were added
  11. stirringby stirring for 12 hours at room temperature
  12. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-a3cf3055e7084903af2ae88119e9ff15
Source dataset
uspto-grants-2011_10
Patent number
US08030498B2

Linked notes

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