Triethylamine → Methyl 4-(1-methanesulfonylamino-1-methylethyl)benzoate

HRID 2411192Notes

Reaction equation

HRID 2411192 reaction equation
[NH2:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>ClCCl>[CH3:22][S:23]([NH:1][C:2]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1)([CH3:3])[CH3:4])(=[O:25])=[O:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57572309Methyl 4-(1-amino-1-methylethyl)benzoate

Product 1

HCID 71252533Methyl 4-(1-methanesulfonylamino-1-methylethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-(1-amino-1-methylethyl)benzoate (200 mg) and triethylamine (0.30 mL) were dissolved in dichloromethane (10 mL), methanesulfonyl chloride (88 μL) was added under ice-cooling, and the mixture was stirred at the same temperature for 30 min and at room temperature for 2 hr. After completion of the reaction, the solvent was evaporated, 0.5N hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (252 mg).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. addition0.5N hydrochloric acid was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-8b6ba91e240f4d0d9a2833cb6411b75e
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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