HCID 21914731, compound → HCID 21914837, compound

HRID 2117868Notes

Reaction equation

HRID 2117868 reaction equation
[OH:1][CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[S:6][CH:7]=1>C(Cl)(Cl)Cl.CO.[O-2].[Mn+4].[O-2]>[CH:2]([C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:13])[O:10][CH2:11][CH3:12])[S:6][CH:7]=1)=[O:1]

Participants

5

Reactant 1

HCID 21914731HCID 21914731, compound

Product 1

HCID 21914837HCID 21914837, compoundYield 106.4%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalyst2×HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixed solution of ethyl 4-(hydroxymethyl)-1,3-thiazol-2-ylcarbamate (446 mg) in chloroform (30 ml) and methanol (3 ml) was added portionwise manganese (IV) oxide chemicals treated (1.92 g) at room temperature. After the mixture was stirred at the same temperature for 2 hours, then treated manganese (IV) oxide chemicals (250 mg) was added again to the solution, and it was stirred at 50° C. for 3 hours. Manganese (IV) oxide was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10 g) using a mixed solvent of hexane and ethyl acetate (4:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give colorless powder (470 mg, 106.4%).

Workup

  1. additiontreated (1.92 g) at room temperature
  2. stirringwas stirred at 50° C. for 3 hours
  3. customManganese (IV) oxide was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (10 g)
  6. additionThe fractions containing the objective compound
  7. customwere collected
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5228cc6187cc43fda3afe8c343c633aa
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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