Water → 4-Oxazol-5-yl-benzenethiol

HRID 18496Notes

Reaction equation

HRID 18496 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([S:12](Cl)(=O)=O)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([SH:12])=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 27764154-(1,3-Oxazol-5-yl)benzenesulphonyl chloride

Product 1

HCID 685864504-Oxazol-5-yl-benzenethiolYield 89.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-oxazol-5-yl-benzenesulfonyl chloride (1 g) in THF (20 ml) was added triphenylphosphine (4.3 g). After stirring at RT for 10 minutes water (2 ml) was added and the reaction was stirred for a further 20 minutes. The reaction was evaporated under reduced pressure and the residue dissolved in EtOAc. The EtOAc solution was extracted with 1M NaOH (×3), the basic extractions were combined, the pH adjusted to 3 using 1M HCl and then re-extracted with EtOAc (×3). The EtOAc fractions were combined and washed with brine, dried (MgSO4) and evaporated under reduced pressure to give the subtitle compound as a green solid (0.65 g).

Workup

  1. additionwas added
  2. customThe reaction was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in EtOAc
  4. extractionThe EtOAc solution was extracted with 1M NaOH (×3)
  5. extractionthe basic extractions
  6. extractionre-extracted with EtOAc (×3)
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-21627b31a7604ea3a37ecb8c1bea554f
Source dataset
uspto-grants-2010_06
Patent number
US07741360B2

Reaction notes

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