Bromine → HCID 13914095, compound

HRID 414258Notes

Reaction equation

HRID 414258 reaction equation
[CH:1]([S:4][C:5]1[S:6][CH:7]=[C:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[N:9]=1)([CH3:3])[CH3:2].[Br:15]Br.S([O-])(O)=O.[Na+]>CCOCC>[CH:1]([S:4][C:5]1[S:6][C:7]([Br:15])=[C:8]([O:10][S:11]([CH3:14])(=[O:12])=[O:13])[N:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 13914034HCID 13914034, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13914095HCID 13914095, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.5 g of 2-isopropylthio-4-methylsulfonyloxy-1,3-thiazole was dissolved in 50 ml of ether, and 0.8 ml of bromine was added dropwise to the solution keeping the temperaure below 0° C. After the addition, the solution was stirred at room temperature for 2 hours, then 5% solution of sodium hydrogen sulfite was added thereto to separate ether layer, which was washed with water and dried over anhydrous sodium sulfate, followed by concentration to an oil. The oil was purified by silica-gel column chromatography to obtain 3.7 g of the objective compound as a yellow oil (yield: 80.7%).

Workup

  1. customthe temperaure below 0° C
  2. additionAfter the addition
  3. customto separate ether layer, which
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationfollowed by concentration to an oil
  7. customThe oil was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-cedf919e20114f0ea43e122c52f8d608
Source dataset
uspto-grants-1988_12
Patent number
US04791127

Reaction notes

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