HCID 21914731, compound → HCID 21914837, compound

HRID 1246458Notes

Reaction equation

HRID 1246458 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-d99145b84e0344b8b2e4497e0b87da62
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

Loading…