Water → HCID 23513330, compound

HRID 354234Notes

Reaction equation

HRID 354234 reaction equation
[CH2:1]([SH:3])[CH3:2].O.C(=O)([O-])[O-].[K+].[K+].Cl[C:12]1[C:22](Cl)=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH3:24])[C:13]=1[C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1>CN(C=O)C>[CH2:1]([S:3][C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:14]([CH3:24])[C:13]=1[C:25]1[O:29][N:28]=[C:27]([CH3:30])[CH:26]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 9948737HCID 9948737, compound

Product 1

HCID 23513330HCID 23513330, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 250-ml round-bottomed flask were placed 0.311 g of ethyl mercaptan, 0.018 g of water and 6 ml of DMF, and then 0.346 g of potassium carbonate and 0.314 g of ethyl 4,5-dichloro-2-methyl-3-(3-methylisoxazol-5-yl)benzoate were adder The resulting mixture was stirred with a magnetic stirrer at room temperature for 6 hours under the irradiation of 40W fluorescent light. The reaction solution was poured into 25 ml of ice-water, and extracted with 25 ml of diethyl ether. The organic layer was washed with water, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained crude product was purified on silica gel column chromatography (elution with n-hexane/ethyl acetate=95/5) to give 0.132 g of the title compound as white crystals. Melting point: 39-40° C.

Workup

  1. customInto a 250-ml round-bottomed flask were placed
  2. extractionextracted with 25 ml of diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe obtained crude product
  7. customwas purified on silica gel column chromatography (elution with n-hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-eecc8139354d42418ec621b09a9847ce
Source dataset
uspto-grants-2004_06
Patent number
US06756497B1

Reaction notes

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