Hydrogen Peroxide → HCID 66720698, compound

HRID 1639517Notes

Reaction equation

HRID 1639517 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][CH3:8])=[N:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH:15]O>C(O)(=O)C>[NH2:1][C:2]1[S:6][C:5]([S:7]([CH3:8])=[O:15])=[N:4][C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 25808447HCID 25808447, compound

Product 1

HCID 66720698HCID 66720698, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-amino-2-(methylsulfanyl)-4-phenylthiazole (305 mg, 1.37 mmol) in acetic acid (3.0 ml) was added aqueous hydrogen peroxide (660 μl, 30% wt, 6.9 mmol) dropwise at ambient temperature. After 4 hr the mixture was partitioned between dichloromethane (60 ml) and water (60 ml). The organic phase was separated, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded pure 5-amino-2-(methylsulfinyl)-4-phenylthiazole (285 mg, 87%).

Workup

  1. customdropwise at ambient temperature
  2. customAfter 4 hr the mixture was partitioned between dichloromethane (60 ml) and water (60 ml)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa04fdcc077146b994e8fe3e603cbdf6
Source dataset
uspto-grants-2012_02
Patent number
US08110568B2

Reaction notes

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