Benzoyl Peroxide → HCID 178429524, compound

HRID 577035Notes

Reaction equation

HRID 577035 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.BrN1C(=O)CCC1=O.C1(C(OOC(=O)C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:34][C:35]1[N:40]=[C:39]([SH:41])[N:38]=[C:37]([OH:42])[CH:36]=1>C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>[CH3:34][C:35]1[N:40]=[C:39]([S:41][CH2:1][C:2]2[S:3][C:4]([CH3:7])=[CH:5][N:6]=2)[N:38]=[C:37]([OH:42])[CH:36]=1

Participants

7

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 77837Thiazole, 2,5-dimethyl-HCID 178429541HCID 178429541, compound

Product 1

HCID 178429524HCID 178429524, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To CCl4 (100 mL) in a 250 mL round bottom flask were added 2,5-dimethyl-1,3-thiazole (1.7 g, 15 mmol), 1-bromopyrrolidine-2,5-dione (2.94 g, 16.5 mmol), and benzoyl benzenecarboperoxoate (180 mg, 0.75 mmol). The reaction mixture was heated at 80° C. for 4 hours. The solvent was then removed under vacuum. The crude product was dissolved in ethanol (30 mL). 6-methyl-2-sulfanylpyrimidin-4-ol (700 mg, 5 mmol) and triethylamine (1.4 mL) were added, and the mixture was stirred at room temperature for 2 hours. After removal of the solvent, the crude product was purified by column chromatography (0-8% methanol in DCM) to provide the title compound as a white solid (480 mg, 40% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.25 (s, 3H), 2.50 (s, 3H), 4.56 (s, 2H), 6.03 (br, 1H), 7.55 (s, 1H); M+ 254.

Workup

  1. customThe solvent was then removed under vacuum
  2. dissolutionThe crude product was dissolved in ethanol (30 mL)
  3. customAfter removal of the solvent
  4. customthe crude product was purified by column chromatography (0-8% methanol in DCM)

Sources & evidence

ORD record
ord-80c825c6ea634771b98417acdf1c2b14
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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