Methyl p-toluenesulfonate → HCID 11669012, compound

HRID 2246756Notes

Reaction equation

HRID 2246756 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:16]=[CH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:7]=1.[C:18]1([CH3:29])[CH:23]=[CH:22][C:21]([S:24]([O:27]C)(=[O:26])=[O:25])=[CH:20][CH:19]=1>CO>[C:18]1([CH3:29])[CH:19]=[CH:20][C:21]([S:24]([O-:27])(=[O:25])=[O:26])=[CH:22][CH:23]=1.[CH2:13]([O:12][C:10]([C:9]1[CH:15]=[CH:16][C:6]([O:5][CH2:4][CH2:3][N+:2]([CH3:18])([CH3:1])[CH3:17])=[CH:7][CH:8]=1)=[O:11])[CH3:14]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 23160726HCID 23160726, compound

Product 1

HCID 11669012HCID 11669012, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

25.0 g (0.11 mol) of the ethyl 4-(2-dimethylaminoethoxy)benzoate obtained in Comparative Example 1 were dissolved in 250 mL of methanol in a nitrogen atmosphere. After adding 23.6 g (0.13 mol) of methyl p-toluenesulfonate while stirring at room temperature, the solution was stirred for 2 hours while heating to 50° C. After distilling off the solvent, the resulting residue was recrystallized from a mixed solvent of 100 mL of methanol and 500 mL of ethyl acetate to obtain 35.9 g of the target substance (yield: 81%).

Workup

  1. stirringthe solution was stirred for 2 hours
  2. temperaturewhile heating to 50° C
  3. distillationAfter distilling off the solvent
  4. customthe resulting residue was recrystallized from a mixed solvent of 100 mL of methanol and 500 mL of ethyl acetate
  5. customto obtain 35.9 g of the target substance (yield: 81%)

Sources & evidence

ORD record
ord-fa8d8d511b3e4d7c8b4c6f383a7b50f9
Source dataset
uspto-grants-2010_03
Patent number
US07687546B2

Reaction notes

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