2-Naphthalenesulfonyl chloride → HCID 15388896, compound

HRID 744728Notes

Reaction equation

HRID 744728 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].O1[CH2:16][CH2:15][CH2:14][CH2:13]1.[CH:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][C:18]=1[S:27](Cl)(=[O:29])=[O:28]>C(N(CC)CC)C>[CH:13]1[C:26]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:27]([N:1]([S:27]([C:18]1[CH:19]=[CH:20][C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:17]=1)(=[O:29])=[O:28])[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 71252-Naphthalenesulfonyl chloride2×HCID 8028TetrahydrofuranHCID 78274Benzoic acid, 3-amino-, methyl ester

Product 1

HCID 15388896HCID 15388896, compoundYield 140.5%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 1.0 g of methyl 3-aminobenzoate (6) (6.62 mmol) in 10 mL of tetrahydrofuran containing 2 mL (14.4 mmol) of triethylamine was added 1.58 g (6.96 mmol) of 2-napthalenesulfonyl chloride. After 10 min, 100 mg of N,N-dimethylaminopyridine was added. After 15 min, another 600 mg of 2-napthalenesulfonyl chloride was added. After stirring for 30 min, the reaction mixture was quenched with 2N HCl and then extracted into ether. The ethereal phase was washed sequentially with water and saturated NaHCO3, then dried (MgSO4), concentrated, and triturated with ether/petroleum ether to give 2.6 g of the title compound as a colorless powder: 1H-NMR (CDCl3, 200 MHz) δ8.46 (s, 2H), 8.13 (d, 1H, J=7.8 Hz), 7.92-8.04 m, 8H), 7.59-7.75 (m, 5H), 7.42 (t, 1H, J=8 Hz), 7.22 (d, 1H, J=7.6 Hz), 3.80 (s, 3H).

Workup

  1. waitAfter 15 min
  2. customthe reaction mixture was quenched with 2N HCl
  3. extractionextracted into ether
  4. washThe ethereal phase was washed sequentially with water and saturated NaHCO3
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customtriturated with ether/petroleum ether

Sources & evidence

ORD record
ord-af24aa503d584ecbb43e6ac1be9bbb54
Source dataset
uspto-grants-1996_09
Patent number
US05559150

Reaction notes

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