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

HRID 1157932Notes

Reaction equation

HRID 1157932 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 l of a water:methanol=1:1 mixed solvent at room temperature, 408 g of Oxone® was gradually added over a period of 30 minutes while stirring. Stirring was continued for 24 hours at room temperature, and then the reaction mixture was poured into a mixture of 10 l of ethyl acetate and 10 l of water. The organic layer was washed with 5 l of brine and dried over anhydrous magnesium sulfate. The desiccant was filtered out and the filtrate was concentrated under reduced pressure to obtain the target compound (37.6 g) as a colorless solid.

Workup

  1. stirringStirring
  2. washThe organic layer was washed with 5 l of brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe desiccant was filtered out
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6044ba0028845bf96f2e8807fec72b9
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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