Triethylamine → Ethyl 2-[4-(Methylsulfonamido)phenyl]acetate

HRID 572923Notes

Reaction equation

HRID 572923 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl>[CH3:21][S:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 10038092Ethyl 2-[4-(Methylsulfonamido)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of ethyl 2-(4-aminophenyl)acetate (500 mg, 2.79 mmol) and triethylamine (0.58 mL, 4.18 mmol) in dichloromethane (30 mL) was added methanesulfonyl chloride (0.24 mL, 3.07 mmol) dropwise at room temperature and stirred overnight. The mixture was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by a standard method to give desired compound. LC-MS: m/z (M+H)=258.3

Workup

  1. washThe mixture was washed with brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by a standard method

Sources & evidence

ORD record
ord-fb2d1e9b58c144f7bd732f22ef461a7e
Source dataset
uspto-grants-2015_05
Patent number
US09029531B2

Reaction notes

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