Hydrogen Peroxide → 5-Amino-2-(tert-butylsulfinyl)-4-phenylthiazole

HRID 1296186Notes

Reaction equation

HRID 1296186 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH:18]O>C(O)(=O)C>[NH2:1][C:2]1[S:6][C:5]([S:7]([C:8]([CH3:11])([CH3:9])[CH3:10])=[O:18])=[N:4][C:3]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 58911918HCID 58911918, compound

Product 1

HCID 667209965-Amino-2-(tert-butylsulfinyl)-4-phenylthiazole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 5-amino-2-(tert-butylsulfanyl)-4-phenylthiazole (102 mg, 385 μmol) in acetic acid (5.0 ml) was added aqueous hydrogen peroxide (218 μl, 30% wt, 1.9 mmol) dropwise at ambient temperature. After 5 hr the mixture was partitioned between dichloromethane (50 ml) and water (50 ml). The aqueous phase was separated and extracted with dichloromethane (20 ml). The combined organic phases were washed with saturated aqueous sodium bicarbonate, dried over sodium sulfate, filtered and concentrated in vacuo to yield essentially pure 5-amino-2-(tert-butylsulfinyl)-4-phenylthiazole (110 mg, quant.).

Workup

  1. customdropwise at ambient temperature
  2. customAfter 5 hr the mixture was partitioned between dichloromethane (50 ml) and water (50 ml)
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane (20 ml)
  5. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cd250d104ae418e9d1064945c73bcc7
Source dataset
uspto-grants-2007_07
Patent number
US07244851B2

Reaction notes

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