Di-tert-butyl peroxide → HCID 68939753, compound

HRID 2218731Notes

Reaction equation

HRID 2218731 reaction equation
[O:1]=[S:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[CH2:3]1.C([O:33]OC(C)(C)C)(C)(C)C>C(Cl)Cl>[O:1]=[S:2]1(=[O:33])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH:13][C:14]2[CH:15]=[C:16]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=2)[C:5]2[CH:25]=[CH:26][CH:27]=[CH:28][C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 8033Di-tert-butyl peroxideHCID 68940823HCID 68940823, compound

Product 1

HCID 68939753HCID 68939753, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve N-[3-(10-oxo-10,11-dihydro-10λ4-thia-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide (35 mg, 0.085 mmol) in 5 mL of methylene chloride at ambient temperature. Add 300 mg of silica gel followed by t-butylperoxide (0.012 mL, 0.085 mmol). Stir overnight, filter and evaporate. Recrystallize from 1:1 ether:pentane to obtain 10.6 mg of the product as a yellow solid. 1H N (CDCl3) δ8.91 (b, 1H), 7.85 (m, 1H), 7.57 (m, 1H), 7.55 (m, 1H), 7.35 (m, 1H), 7.25-7.15 (m, 2H), 7.10 (m, 1H), 7.02 (m, 1H), 7.00-6.95 (m, 1H), 6.30 (d, 2H), 6.15 (d, 1H), 5.25 (t, 1H), 4.40 (t, 1H), 2.80 (s, 311). MS [EI+] 424 (M−H).

Workup

  1. additionAdd 300 mg of silica gel
  2. filtrationfilter
  3. customevaporate
  4. customRecrystallize from 1:1 ether

Sources & evidence

ORD record
ord-90ae9a6d5a3d4801ac8120e751161553
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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