Sulfuric Acid → HCID 58911918, compound

HRID 1296185Notes

Reaction equation

HRID 1296185 reaction equation
[NH2:1][C:2]1[S:6][C:5]([SH:7])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:14](O)([CH3:17])([CH3:16])[CH3:15].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O>[NH2:1][C:2]1[S:6][C:5]([S:7][C:14]([CH3:17])([CH3:16])[CH3:15])=[N:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-Butanol2×HCID 516892Sodium BicarbonateHCID 178509330HCID 178509330, compound

Product 1

HCID 58911918HCID 58911918, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 5-amino-2-mercapto-4-phenylthiazole (210 mg, 1.01 mmol) in water (1.0 ml) and tert-butanol (82 mg, 1.1 mmol) was added concentrated sulfuric acid (3.0 ml) with cooling to ca. 20° C. After 1.5 hr at ambient temperature a further portion of tert-butanol in water (300 μl, 1.0 M, 300 μmol) was added. After 1.5 hr the mixture was poured into excess aqueous sodium bicarbonate and extracted three times into dichloromethane (total 120 ml). The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 5-amino-2-(tert-butylsulfanyl)-4-phenylthiazole (220 mg, 82%).

Workup

  1. extractionextracted three times into dichloromethane (total 120 ml)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a460627ef92400d9d6c9b957bb5939d
Source dataset
uspto-grants-2007_07
Patent number
US07244851B2

Reaction notes

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