Dimethylformamide → HCID 10670178, compound

HRID 1768717Notes

Reaction equation

HRID 1768717 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[O:4][C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].CN(C=O)C.C([O-])([O-])=O.[K+].[K+].Cl[CH2:23][N:24]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][C:30]([O:39][CH3:40])=[CH:31][C:32]=2[CH:36]([CH3:38])[CH3:37])[S:25]1(=[O:27])=[O:26]>O>[Cl:1][C:2]1[C:3](=[O:10])[O:4][C:5]([CH3:9])=[CH:6][C:7]=1[O:8][CH2:23][N:24]1[C:34](=[O:35])[C:33]2[C:28](=[CH:29][C:30]([O:39][CH3:40])=[CH:31][C:32]=2[CH:36]([CH3:38])[CH3:37])[S:25]1(=[O:26])=[O:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 99951732-(Chloromethyl)-4-isopropyl-6-methoxybenzo[D]isothiazol-3(2H)-one 1,1-dioxideHCID 54686092HCID 54686092, compound

Product 1

HCID 10670178HCID 10670178, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-chloro-4-hydroxy-6-methyl-2H-pyran-2-one (0.493 g, 3.07 mmol), DMF and K2CO3 (0.467 g, 3.38 mmol) was stirred at room temperature under N2 for 0.5 hours then 2-chloromethyl-4-isopropyl-6-methoxysaccharin (0.978 g, 3.22 mmol) was added in one portion. The mixture was stirred at room temperature for 3 hours, and then at 75° C. for 3 hours. The mixture was poured into water, extracted with ethyl acetate and the organic layer was washed with brine and dried. The solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 30% ethyl acetate/hexane to afford 0.25 g (18.1%) of 2-(3-chloro-6-methyl-2-oxo-2H-pyran-4yl)oxymethyl-4-isopropyl-6-methoxysaccharin, m.p. 182.5°-183.5° C. after recrystallization from ether/hexane.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. waitat 75° C. for 3 hours
  3. extractionextracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by column chromatography on silica eluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-bcbebfb34bf744f28e210c064949ec78
Source dataset
uspto-grants-1995_01
Patent number
US05378720

Reaction notes

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