m-Chloroperbenzoic acid → HCID 58079292, compound

HRID 2094824Notes

Reaction equation

HRID 2094824 reaction equation
BrC1C=CC(S[CH2:9][C:10]([C:16]2[S:20][CH:19]=[N:18][CH:17]=2)([OH:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=CC=1.Cl[C:22]1[CH:27]=CC=C(C(OO)=O)[CH:23]=1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:14][C:11]1([C:10]2([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[CH2:9][O:15]2)[CH2:12][CH2:27][CH2:22][CH2:23][CH2:13]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 66725571HCID 66725571, compound

Product 1

HCID 58079292HCID 58079292, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1.00 g (2.7 mmol) of 1-[(4-bromophenyl)sulphanyl]-3,3-dimethyl-2-(1,3-thiazol-5-yl)butan-2-ol dissolved in 100 ml of dichloromethane was added, at room temperature, 0.70 g (4.0 mmol) of meta-chloroperbenzoic acid, and the reaction mixture was stirred at room temperature for 16 h. After addition of saturated aqueous sodium hydrogen carbonate solution, the organic phase was removed and the aqueous phase was extracted with dichloromethane. The combined organic phases were dried in the sodium sulphate, filtered and concentrated. The crude product was subsequently purified by column chromatography (1:1 tert-butyl methyl ether/petroleum ether). This gave 0.80 g (76%) of compound 8 and 0.25 g (23%) of compound 9.

Workup

  1. additionwas added, at room temperature
  2. customthe organic phase was removed
  3. extractionthe aqueous phase was extracted with dichloromethane
  4. dry with materialThe combined organic phases were dried in the sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was subsequently purified by column chromatography (1:1 tert-butyl methyl ether/petroleum ether)

Sources & evidence

ORD record
ord-bc3b277e660f44778189c794229a36a8
Source dataset
uspto-grants-2013_05
Patent number
US08445691B2

Reaction notes

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