Water → Ethyl 3-[(propane-1-sulfonyl)amino]benzoate

HRID 1261025Notes

Reaction equation

HRID 1261025 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1)[CH3:2].N1C=CC=CC=1.[CH2:19]([S:22](Cl)(=[O:24])=[O:23])[CH2:20][CH3:21].O>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][S:22]([CH2:19][CH2:20][CH3:21])(=[O:24])=[O:23])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 11400Ethyl 3-aminobenzoateHCID 662791-Propanesulfonyl chloride

Product 1

HCID 58087920Ethyl 3-[(propane-1-sulfonyl)amino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-amino-benzoic acid ethyl ester (74, 5.0 g, 0.030 mol) in methylene chloride (30.0 mL) were added pyridine (3.67 mL, 0.045 mol) and propane-1-sulfonyl chloride (3.75 mL, 33.0 mmol). The reaction was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated. The desired compound was isolated by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a white solid (75, 6.0 g, 74.1%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b66a10135837443ab98ac396bfd4995d
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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