Methanethiol → HCID 86759468, compound

HRID 354233Notes

Reaction equation

HRID 354233 reaction equation
CS.C(=O)([O-])[O-].[K+].[K+].ClC1C(Cl)=CC(C(OC)=O)=C(C)C=1C1CCON=1.Cl[C:28]1[C:29]([CH3:44])=[C:30]([C:39]2[CH2:43][CH2:42][O:41][N:40]=2)[C:31]([CH3:38])=[C:32]([CH:37]=1)[C:33]([O:35][CH3:36])=[S:34]>CN(C=O)C>[O:41]1[CH2:42][CH2:43][C:39]([C:30]2[C:31]([CH3:38])=[C:32]([CH:37]=[CH:28][C:29]=2[CH3:44])[C:33]([O:35][CH3:36])=[S:34])=[N:40]1

Participants

6

Reactant 4

HCID 878MethanethiolHCID 11430Potassium CarbonateHCID 9925957HCID 9925957, compoundHCID 86759469HCID 86759469, compound

Product 1

HCID 86759468HCID 86759468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10 ml of degassed DMF was placed in a colorless, transparent glass container, and 420 mg of methyl mercaptan was blown in to dissolve. Then 600 mg of potassium carbonate and 500 mg of methyl 4,5-dichloro-3-(2-isoxazolin-3-yl)-2-methylbenzoate were added one by one. The resulting solution was stirred with a Teflon magnetic stirrer at room temperature with light shielded under the nitrogen atmosphere. After stirring it for an hour, it was confirmed by NMR that methyl 5-chloro-3-(2-isoxazolin-3-yl)-2-methyl-4-methylthiobenzoate was a major product. Succeedingly, the reaction system was stirred at 40° C. for 2 hours, while irradiating with white fluorescent light. The reaction solution was poured into ice-water, and extracted with ether-chloroform (5:1) and then with ether. The organic layers were washed with water, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified on silica gel column chromatography (elution with n-hexane/ethyl acetate=95/5) to give 424 mg of the title compound as white crystals. Melting point: 109-111° C.

Workup

  1. dissolutionto dissolve
  2. stirringAfter stirring it for an hour
  3. stirringSucceedingly, the reaction system was stirred at 40° C. for 2 hours
  4. customwhile irradiating with white fluorescent light
  5. extractionextracted with ether-chloroform (5:1)
  6. washThe organic layers were washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified on silica gel column chromatography (elution with n-hexane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-04fe78f671064985bc3dc378cb5fe41d
Source dataset
uspto-grants-2004_06
Patent number
US06756497B1

Reaction notes

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