1,2-Dimethoxyethane → HCID 20510475, compound

HRID 1758021Notes

Reaction equation

HRID 1758021 reaction equation
[OH:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][C:3]1=[O:13].COCCOC.[F:20][C:21]([F:27])([F:26])[S:22](Cl)(=[O:24])=[O:23].C(N(CC)CC)C>C(Cl)Cl>[F:20][C:21]([F:27])([F:26])[S:22]([O:1][N:2]1[C:7](=[O:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[O:4][C:3]1=[O:13])(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 2249803-hydroxy-2h-1,3-benzoxazine-2,4(3h)-dione

Product 1

HCID 20510475HCID 20510475, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Trifluoromethanesulfonyloxy-1,3-benzoxazine-2,4-dione was prepared by the following procedure. To a dried flask with a stirrer, under nitrogen, were added 3-hydroxy-1,3-benzoxazine-2,4-dione (3.35 g, 18.7 mmol) (U.S. Pat. 2,714,105) and 100 mL of dried DME. The mixture was held at -15°, and trifluoromethanesulfonyl chloride (2.00 mL, 18.7 mmol) followed by triethylamine (3.00 mL, 22 mmol) were added dropwise by syringe. After warming to room temperature, the reaction mixture was diluted with 200 mL of methylene chloride and washed successively with water, 2 percent aqueous sodium bicarbonate, and water, and then dried. Evaporation of the solvent gave 5.13 g of white solid: mp 73°-76°. Recrystallization from methylene chloride-hexane gave 3.60 g (62%) of 3-trifluoromethanesulfonyloxy-1,3-benzoxazine-2,4-dione: mp 74°-76°; uv (CH3CN) 237 (11,100), and 289 nm (2180); ir (KBr) 1800 (s), 1742 (vs), 1612 (m), 1465 (s), 1448 (s), 1342 (m), 1228 (vs), 1126 (m), 1090 (m); mass spectrum 310.9686 (calcd for C9H4NO6F3S: 310.9701); 217,0098 (calcd for C9H4O3F3 : 217.0112); 120.0200 (calcd for C7H4O2 : 120.0211). A second crop of product, 0.70 g, raised the overall yield to 73.9%.

Workup

  1. customwas held at -15°
  2. additionwere added dropwise by syringe
  3. washwashed successively with water, 2 percent aqueous sodium bicarbonate, and water
  4. customdried
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-6e21423200464e269254ceddc44091de
Source dataset
uspto-grants-1983_02
Patent number
US04371605

Reaction notes

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