Methanol → Methyl 4-amino-2-(methylsulfonyl)thiazole-5-carboxylate

HRID 1161514Notes

Reaction equation

HRID 1161514 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:9][C:8](SC)=[N:7][C:6]=1[NH2:12])=[O:4].[CH3:13]O.O[O:16][S:17]([O-:19])=O.[K+]>O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:9][C:8]([S:17]([CH3:13])(=[O:19])=[O:16])=[N:7][C:6]=1[NH2:12])=[O:4]

Participants

6

Reactant 3

HCID 887MethanolHCID 609212Methyl 4-amino-2-(methylsulfanyl)-1,3-thiazole-5-carboxylateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 59511825Methyl 4-amino-2-(methylsulfonyl)thiazole-5-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

After adding 45.2 g of 4-amino-2-methylsulfanylthiazole-5-carboxylic acid methyl ester [CAS No. 60093-05-2] to 2 liters of a water:methanol=1:1 mixed solvent at room temperature, 408 g of Oxone was added in small portions over a period of 30 minutes with stirring. The mixture was stirred at room temperature for 24 hours, and then poured into a mixture of 10 liters of ethyl acetate and 10 liters of water. After washing the organic layer with 5 liters of saturated brine, it was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (37.6 g) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 24 hours
  2. washAfter washing the organic layer with 5 liters of saturated brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8868a0534fa4200ad72ce3db3b9ac99
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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