Trifluoroacetic anhydride → HCID 57552585, compound

HRID 2205429Notes

Reaction equation

HRID 2205429 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-4c8b561fc9f340888b838320822ec96b
Source dataset
uspto-grants-2016_06
Patent number
US09371298B2

Reaction notes

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