Trifluoroacetic anhydride → HCID 57552585, compound

HRID 335516Notes

Reaction equation

HRID 335516 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([O:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][S:8][C:9]=1SC)=[O:4].OO.N[C:20](N)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[S:36]([O-:39])(O)=[O:37].[Na+]>O>[CH3:1][O:2][C:3]([C:5]1[C:6]([O:12][C:13]([O:15][CH3:16])=[O:14])=[N:7][S:8][C:9]=1[S:36]([CH3:20])(=[O:39])=[O:37])=[O:4]

Participants

6

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 31294Carbamide PeroxideHCID 23665763Sodium BisulfiteHCID 57552583HCID 57552583, compound

Product 1

HCID 57552585HCID 57552585, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

The 3-Methoxycarbonyloxy-5-methylsulfanyl-isothiazole-4-carboxylic acid methyl ester slurry was cooled to 0° C., and urea hydrogen peroxide addition compound (2.8 equiv, 12.8 g) was added. Trifluoroacetic acid anhydride (2.8 equiv, 19.2 mL, 28.4 g) was added dropwise over 20 minutes. The mixture stirred at 0° C. for 45 minutes, and quenched with sodium hydrogen sulfite (2.0 equiv, 10.0 g) in water (90 mL, 9 volumes) and stirred at 25° C. Most of the acetonitrile was removed under vacuum, then the aqueous residue was extracted once with 100 mL and once again with 50 mL dichloromethane to provide 5-Methanesulfonyl-3-methoxycarbonyloxy-isothiazole-4-carboxylic acid methyl ester.

Workup

  1. additionwas added
  2. stirringstirred at 25° C
  3. customMost of the acetonitrile was removed under vacuum
  4. extractionthe aqueous residue was extracted once with 100 mL and once again with 50 mL dichloromethane

Sources & evidence

ORD record
ord-86450efc4b144da38400d2e809b29538
Source dataset
uspto-grants-2014_11
Patent number
US08884025B2

Reaction notes

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