2-Naphthalenesulfonyl chloride → Benzoic acid, 3-[(2-naphthalenylsulfonyl)amino]-, ethyl ester

HRID 2304448Notes

Reaction equation

HRID 2304448 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11](Cl)(=[O:13])=[O:12].[NH2:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(N(CC)CC)C>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:15][C:16]1[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoate

Product 1

HCID 8823764Benzoic acid, 3-[(2-naphthalenylsulfonyl)amino]-, ethyl esterYield 103.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

34.3 g (0.15 mol) of 2-naphthalenesulfonyl chloride, dissolved in 250 ml of tetrahydrofuran, were added dropwise to 25 g (0.15 mol) of ethyl 3-aminobenzoate and 63 ml (0.45 mol) of triethylamine in 400 ml of tetrahydrofuran at 0° C. The mixture was then heated to reflux for 1 h. The organic solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and water. The ethyl acetate phase was dried and concentrated in vacuo. 55 g (100%) of the product were obtained.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1 h
  3. customThe organic solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. dry with materialThe ethyl acetate phase was dried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2fa41c25dc948c4b291815954039736
Source dataset
uspto-grants-2002_08
Patent number
US06436925B1

Reaction notes

Loading…