Pyrazole → 4-Methoxyimino-5-methyl-6-(1-ethyl-5-phenacyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide

HRID 1067

Reaction equation

HRID 1067 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([C:17]3[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=3[OH:22])=[O:16])[C:12]=2[CH3:14])[S:7](=[O:26])(=[O:25])[CH2:6][CH2:5]1.N1C=CC=N1.[CH2:32](Br)[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][N:3]=[C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:15]([C:17]3[CH:18]=[N:19][N:20]([CH2:23][CH3:24])[C:21]=3[O:22][CH2:32][C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:34])=[O:16])[C:12]=2[CH3:14])[S:7](=[O:25])(=[O:26])[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 178418231HCID 178418231, compound

Product 1

HCID 867521704-Methoxyimino-5-methyl-6-(1-ethyl-5-phenacyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxideYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.4 Gram (1.1 mmol) of 4-methoxyimino-5-methyl-6-(1-ethyl-5-hydroxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide corresponding to pyrazole derivative (I-H), 0.23 g (1.2 mmol) of phenacyl bromide corresponding to compound B-A-Hal and 0.15 g of potassium carbonate were added to 10 ml of acetone, and the mixture was stirred under heat for 8 hours. Insolubles were removed by filtration, and then the acetone was distilled off. The residue was dissolved in ethyl acetate, and the mixture was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. The ethyl acetate was distilled off under reduced pressure, and the residue was subjected to column chromatography (hexane/ethyl acetate) to give 4-methoxyimino-5-methyl-6-(1-ethyl-5-phenacyloxypyrazol-4-yl)carbonylthiochroman-1,1-dioxide (Compound Ib-2) at a yield of 52%.

Workup

  1. temperatureunder heat for 8 hours
  2. customInsolubles were removed by filtration
  3. distillationthe acetone was distilled off
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe mixture was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over sodium sulfate
  7. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7676d3f705f64b5888f4950efb2b2f22
Source dataset
uspto-grants-1998_03
Patent number
US05723408

Linked notes

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