Dimethyl Sulfoxide → HCID 54104386, compound

HRID 1905400Notes

Reaction equation

HRID 1905400 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][OH:16])=[CH:4][CH:3]=1.[OH-].[Na+].CS(C)=O.Br[CH2:26][C:27]1[CH:41]=[CH:40][C:30]([C:31]([O:33][CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[O:32])=[CH:29][CH:28]=1>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[N:11]([CH3:12])[N:10]=[C:9]([CH3:13])[C:8]=2[CH:14]=[N:15][O:16][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([O:33][CH:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]3)=[O:32])=[CH:40][CH:41]=2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 20035473HCID 20035473, compoundHCID 57016257HCID 57016257, compound

Product 1

HCID 54104386HCID 54104386, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.0 Grams (0.008 mole) of 5-(4-fluorophenoxy)-1,3-dimethylpyrazole-4-carbaldehyde oxime and 0.5 g (0.0125 mole) of powdery sodium hydroxide were added to 50 ml of dimethyl sulfoxide, and the resulting mixture was stirred for 30 minutes. To this solution was added 2.38 g (0.008 mole) of cyclohexyl 4-bromomethylbenzoate, and reaction was carried out at from 70° to 80° C. for 6 hours. After completion of the reaction, water was added to the reaction solution which was then extracted with ethyl acetate. The ethyl acetate extract was washed with water and dried, and ethyl acetate was removed by evaporation to obtain an oily product. This oily product was column-chromatographed on silica gel to obtain 3.0 g of the desired compound.

Workup

  1. additionTo this solution was added
  2. waitwas carried out at from 70° to 80° C. for 6 hours
  3. additionwas added to the reaction solution which
  4. extractionwas then extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. customethyl acetate was removed by evaporation
  9. customto obtain an oily product
  10. customThis oily product was column-chromatographed on silica gel

Sources & evidence

ORD record
ord-81e6f52b45324512a4fd0363697e89e6
Source dataset
uspto-grants-1989_06
Patent number
US04843068

Reaction notes

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