Triethylamine → Methyl 4-[[2-(dimethylamino)ethyl](methylsulfonyl)amino]benzoate

HRID 1643314Notes

Reaction equation

HRID 1643314 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[CH3:13][N:14]([CH3:28])[CH2:15][CH2:16][NH:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl.C(OCC)(=O)C>[CH3:28][N:14]([CH3:13])[CH2:15][CH2:16][N:17]([S:2]([CH3:1])(=[O:4])=[O:3])[C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57440398Methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate

Product 1

HCID 57857113Methyl 4-[[2-(dimethylamino)ethyl](methylsulfonyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulfonyl chloride (0.105 ml, 1.350 mmol) was added to a stirred solution of triethylamine (0.282 ml, 2.024 mmol) and methyl 4-{[2-(dimethylamino)ethyl]amino}benzoate (0.15 g, 0.675 mmol) in CH2Cl2 (2 ml) and the mixture was stirred at room temperature for overnight. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate, dried over Na2SO4 filtered and the solvent was evaporated under reduced pressure. The product was purified by reversed phase HPLC (20-100% MeCN/H2O with 0.05% TFA). MS cal'd 301 (MH+), exp 301(MH+).

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe product was purified by reversed phase HPLC (20-100% MeCN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-15b1a44f917749b493689231a8a4ada4
Source dataset
uspto-grants-2012_02
Patent number
US08119685B2

Reaction notes

Loading…