Benzoyl Peroxide → HCID 17973804, compound

HRID 747389Notes

Reaction equation

HRID 747389 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12](=[O:23])(=[O:22])[NH:13][C:14]3([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[C:15]=2[CH3:16])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH2:16][C:15]1[C:14]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:13][S:12](=[O:23])(=[O:22])[C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59749387HCID 59749387, compound

Product 1

HCID 17973804HCID 17973804, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-(4-methanesulfonyl-phenyl)-4-methyl-2-thia-1-azaspiro[4.5]dec-3-ene 2,2-dioxide (4.5 g, 12.6 mmol) and N-bromo succinimide (2.5 g, 14 mmol) were stirred in 200 ml CCl4 with a catalytic amount of benzoyl peroxide for 4 hours at 85° C. Then the solvent was evaporated and the residue disolved in dichloromethane, washed with water and NaHCO3 solution, dried (Na2SO4) and evaporated. The solid product was recrystallized from ethanol to yield 4-bromomethyl-3-(4-methanesulfonyl-phenyl)-2-thia-1-aza-spiro[4.5]dec-3-ene 2,2-dioxide (3.7 g, 68%). This product was dissolved in ethanol (20 ml), ethylamine (70% solution in water, 20 ml) was added, the mixture was left at room temperature for 3 hours and evaporated. The residue was dissolved in CH2Cl2, washed with water and extracted with 2 M HCl. After addition of NaOH and extraction with CH2Cl2 the organic layer was dried (Na2SO4) and evaporated. Chromatography on silica (eluent CH2Cl2/EtOH 95:5) yielded 1.50 g (66%) N-ethyl-N-[3-(4-methanesulfonyl-phenyl)-2,2-dioxo-2-thia-1-aza-spiro[4.5]dec-3-en-4-ylmethyl]-amine, shown below. 1H-NMR (CDCl3) δ 8.01 (d, 2H), 7.83 (d, 2 H), 4.81 (s, 1 H), 3.45 (s, 2 H), 3.09 (s, 3 H), 2.54 (q, 2 H), 2.02-1.15 (m, 10 H), 0.96 (t, 3 H).

Workup

  1. customThen the solvent was evaporated
  2. washthe residue disolved in dichloromethane, washed with water and NaHCO3 solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe solid product was recrystallized from ethanol

Sources & evidence

ORD record
ord-25fc2eeea271484fb0ff8184c42e69c0
Source dataset
uspto-grants-2008_07
Patent number
US07396846B2

Reaction notes

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