Benzoyl Peroxide → HCID 59589488, compound

HRID 577244Notes

Reaction equation

HRID 577244 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[CH:7]([OH:9])[CH3:8].[Br:10]N1C(=O)CCC1=O.C1(C(OOC(=O)C2C=CC=CC=2)=O)C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:1][C:2]1[S:6][CH:5]=[N:4][C:3]=1[C:7](=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21313043α,5-Dimethyl-4-thiazolemethanol

Product 1

HCID 59589488HCID 59589488, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 1-(5-methyl-1,3-thiazol-4-yl)ethan-1-ol (1.0 g, 7.0 mmol) in anhydrous carbon tetrachloride (50 mL) was added recrystallized 1-bromopyrrolidine-2,5-dione (1.4 g, 7.7 mmol) and benzoyl benzenecarboperoxoate (170 mg, 0.7 mmol). The mixture was stirred at reflux for 5 hours. After cooling to room temperature, the solid material was removed by filtration. The filtrate was recovered and evaporated. The residue was dried in vacuo, affording 1-[5-(bromomethyl)-1,3-thiazol-4-yl]ethan-1-one (615 mg, 40%). The product was used for the next step without further purification.

Workup

  1. temperatureat reflux for 5 hours
  2. customthe solid material was removed by filtration
  3. customThe filtrate was recovered
  4. customevaporated
  5. customThe residue was dried in vacuo

Sources & evidence

ORD record
ord-e5e9ec420d9a4511a82ae4cd89716519
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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