Hydrochloric Acid → HCID 15228044, compound

HRID 1769430Notes

Reaction equation

HRID 1769430 reaction equation
[OH:1][C:2]1[C:3]([F:16])=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[C:12]([F:15])[C:13]=1[F:14].[C:17](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.Cl>O.CC(C)=O>[CH3:17][O:1][C:2]1[C:3]([F:16])=[C:4]2[C:9](=[O:10])[N:8]([CH3:11])[C:6](=[O:7])[C:5]2=[C:12]([F:15])[C:13]=1[F:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10878985HCID 10878985, compound

Product 1

HCID 15228044HCID 15228044, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The solids from Example 1 were combined with 375 mL of acetone, and 61.08 g of potassium carbonate. With stirring, 55.77 g of dimethyl sulfate was added, and the entire mixture was heated to reflux for 1.5 h. After cooling, 500 mL of water was added and the reaction was acidified with HCl to a pH of 1.0. The mixture was extracted with ethyl acetate and washed with water. After drying with magnesium sulfate and removal of the solvent, 45.08 g of a yellow solid was collected. The solid was assayed as 72% 4-methoxy-3,5,6-trifluoro-N-methylphthalimide. 19F NMR (ppm acetone d6): -133.0 (m), -140.8 (m), -142.6 (m), 1H NMR (ppm acetone d6) 3.05 (s), 4.19 (s).

Workup

  1. temperaturethe entire mixture was heated
  2. temperatureto reflux for 1.5 h
  3. temperatureAfter cooling
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialAfter drying with magnesium sulfate and removal of the solvent, 45.08 g of a yellow solid
  7. customwas collected

Sources & evidence

ORD record
ord-dfa9dfe4a8174900b2178679b95eae94
Source dataset
uspto-grants-1995_01
Patent number
US05380926

Reaction notes

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