Triethylamine → HCID 18470649, compound

HRID 2228496Notes

Reaction equation

HRID 2228496 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][O:7][C:8]1[C:9]([OH:20])=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C>ClCCl>[CH3:6][O:7][C:8]1[C:9]([O:20][S:2]([CH3:1])(=[O:4])=[O:3])=[C:10]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 5319678HCID 5319678, compound

Product 1

HCID 18470649HCID 18470649, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (634 Π, 0.008 mol) was added dropwise to an ice-cooled solution of methyl 3,4-dimethoxy-2-hydroxybenzoate (1.58 g, 0.0075 mol) and triethylamine (1.27 ml, 0.009 mol) in dichloromethane (30 ml) and the reaction then allowed to warm to room temperature, with stirring. The reaction mixture was washed with water (2×25 ml) and the organic layer dried (MgSO4), filtered and evaporated under reduced pressure. The crude product was purified on silica gel eluting with a solvent gradient of diethyl ether:hexane (60:40 to 100:0, v/v) to give the subtitle compound as a colourless oil that crystallised on standing (1.94 g, 90%). MS m/z 308 (MNH4)+.

Workup

  1. customthe reaction
  2. washThe reaction mixture was washed with water (2×25 ml)
  3. dry with materialthe organic layer dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe crude product was purified on silica gel eluting with a solvent gradient of diethyl ether:hexane (60:40 to 100:0

Sources & evidence

ORD record
ord-99c481ed507b43fb8013c0c76ef13686
Source dataset
uspto-grants-2002_07
Patent number
US06417194B1

Reaction notes

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