2-Naphthalenesulfonyl chloride → HCID 2197146, compound

HRID 1758023Notes

Reaction equation

HRID 1758023 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23](Cl)(=[O:25])=[O:24].C1COCC1.C(N(CC)CC)C>C(Cl)Cl>[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[S:23]([O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7])(=[O:24])=[O:25]

Participants

6

Reactant 4

HCID 71252-Naphthalenesulfonyl chlorideHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 10665N-Hydroxyphthalimide

Product 1

HCID 2197146HCID 2197146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-2-Naphthalenesulfonyloxyphthalimide was prepared by the following procedure. To a flask equipped with a stirrer and addition funnel were added N-hydroxyphthalimide (8.15 g, 0.050 mol), 2-naphthalenesulfonyl chloride (11.4 g, 0.050 mol) and 125 mL of THF. A solution of triethylamine (8 mL, 0.058 mol) and 25 mL of THF was added dropwise. After 1 h stirring, the reaction mixture was diluted with 200 mL of methylene chloride and the organic layer was washed successively with water, 3 percent aqueous sodium bicarbonate, and water. The organic layer containing crystallized product was evaporated leaving 16.8 g of an off-white solid. Recrystallization from toluene gave 12.33 g (69.8%) of white, crystalline N-2-naphthalenesulfonyloxyphthalimide: mp 223°-225°; nmr (CDCl3 -DMSO-d6) 8.8-7.7 (m), singlet at 7.9; uv (CH3CN) 220 (67,000), 234 (79,800), 279 (6880), 317 (1825), 331 nm (1950); ir (nujol) 1787 (m), 1737 (s), 1380 (m), 1190 (s), 965 (s); mass spectrum 353.0350 (calcd for C18H11NO5S: m+, 353.0357). Anal. Calcd for C18H11NO5S: C, 61.19; H, 3.14; N, 3.96; O, 22.64; S, 9.07. Found: C, 61.03, 61.01; H, 3.13, 3.35; N, 4.06, 3.98.

Workup

  1. customTo a flask equipped with a stirrer and addition funnel
  2. washthe organic layer was washed successively with water, 3 percent aqueous sodium bicarbonate, and water
  3. additionThe organic layer containing
  4. customcrystallized product
  5. customwas evaporated

Sources & evidence

ORD record
ord-fb7a88c4e39445ef8496f7a6ce8b916d
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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