1,2-Dimethoxyethane → HCID 5142394, compound

HRID 1758020Notes

Reaction equation

HRID 1758020 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].COCCOC.[F:19][C:20]([F:26])([F:25])[S:21](Cl)(=[O:23])=[O:22].C(N(CC)CC)C>C(Cl)Cl>[F:19][C:20]([F:26])([F:25])[S:21]([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:23])=[O:22]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 79000Trifluoromethanesulfonyl chloride

Product 1

HCID 5142394HCID 5142394, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Trifluoromethanesulfonyloxyphthalimide was prepared by the following procedure. To a dried flask equipped with a stirrer, under nitrogen, were added N-hydroxyphthalimide (3.04 g, 18.7 mmol), 60 mL of dried DME, and trifluoromethanesulfonyl chloride (2.00 mL, 18.7 mmol). The mixture was cooled to -15° and triethylamine (3.00 mL, 22 mmol) was added dropwise by syringe. After warming to room temperature, 100 mL of methylene chloride was added and the resulting mixture was washed with 100 mL of 2% aqueous sodium bicarbonate and dried. Evaporation of the solvent gave 4.65 g of crude N-trifluoromethanesulfonyloxyphthalimide: mp 90°-93°. Recrystallization from methylene chloride-hexane gave 2.65 g (48%) of product as shiny white flakes: mp 99°-102°; uv (CH3CN) 220 (47,000), 249 (2090), 297 nm (2290); ir (KBr) 1810 (m), 1750 (vs), 1440 (s), 1240 (s), 1230 (s), 1220 (s), 1115 (m), 940 (m), 860 (m), 695 (s), 585 (m); nmr (CDCl3) 8.10-7.85 (m); 19F nmr (CDCl3) -71.42 ppm (s); mass spectrum 294.9782 (calcd for C9H4NO5F3S: 294.9762).

Workup

  1. customN-Trifluoromethanesulfonyloxyphthalimide was prepared by the following procedure
  2. customTo a dried flask equipped with a stirrer, under nitrogen
  3. temperatureThe mixture was cooled to -15°
  4. washthe resulting mixture was washed with 100 mL of 2% aqueous sodium bicarbonate
  5. customdried
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-61f37cbff8ff4a209a2f21c0cf25af02
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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