Methyl Salicylate → HCID 4316447, compound

HRID 1491560Notes

Reaction equation

HRID 1491560 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[C:8]([O:17][CH3:18])(=[O:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[OH:11].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.COCCOCCN(CCOCCOC)CCOCCOC>[CH3:1][N:2]([CH3:7])[S:3]([O:11][C:10]1[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=1[C:8]([O:17][CH3:18])=[O:16])(=[O:5])=[O:4]

Participants

6

Reactant 3

HCID 4133Methyl SalicylateHCID 11430Potassium CarbonateHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 4316447HCID 4316447, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-CatalystHCID 6342AcetonitrileSolvent

Procedure

Dimethylaminosulphonyl chloride (17.2 g)was added to a mixture of methyl salicylate (15.2 g) and potassium carbonate (27.6 g) in acetonitrile. The mixture was stirred at room temperature for 1 hour. TDA-1 (2.0 g) was added and the mixture stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was filtered off and purified by chromatography eluted with dichloromethane to give methyl 2-(dimethylaminosulphonyloxy)benzoate (17.4 g) as a white solid m.p. 75.5°-76.5° C.

Workup

  1. stirringthe mixture stirred at room temperature for 24 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was triturated with ether
  10. filtrationThe solid was filtered off
  11. custompurified by chromatography
  12. washeluted with dichloromethane

Sources & evidence

ORD record
ord-f32d3364c79f46b2b1bd4fabdb49cb37
Source dataset
uspto-grants-1994_12
Patent number
US05371063

Reaction notes

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