Benzoyl Peroxide → HCID 21866262, compound

HRID 857784Notes

Reaction equation

HRID 857784 reaction equation
[Cl:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[CH3:14])=[N:5][S:4][N:3]=1.C1C(=O)N([Br:22])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[C:6]1[C:2]([Cl:1])=[N:3][S:4][N:5]=1

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 67184N-bromobutanimideHCID 21866306HCID 21866306, compound

Product 1

HCID 21866262HCID 21866262, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-chloro-4-(4-chloro-2-methylphenyl)-1,2,5-thiadiazole (0.211 g, 0.86 mmol), NBS (0.153 g, 0.86 mmol) and benzoyl peroxide (10.4 mg, 0.04 mmol) in carbon tetrachloride (5.0 mL) were refluxed for 1 h. More benzoyl peroxide (10.4 mg, 0.04 mmol) was added and the solution was refluxed for a further 16 h. The resulting suspension was filtered, rinsing with ether. The filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium bicarbonate solution and brine. The ether layer was separated, dried (Na2SO4) and reduced in vacuo. The residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 1–3% EtOAc). 3-[2-(Bromomethyl)-4-chlorophenyl]-4-chloro-1,2,5-thiadiazole was isolated as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 4.51 (s, 2H), 7.43 (s, 2H), 7.55 (s, 1H).

Workup

  1. temperaturewere refluxed for 1 h
  2. temperaturethe solution was refluxed for a further 16 h
  3. filtrationThe resulting suspension was filtered
  4. washrinsing with ether
  5. washThe filtrate was washed with 10% aqueous sodium sulfite, saturated aqueous sodium bicarbonate solution and brine
  6. customThe ether layer was separated
  7. dry with materialdried (Na2SO4)
  8. customThe residue was purified by flash chromatography on silica (eluting with EtOAc/hexanes gradient, 1–3% EtOAc)

Sources & evidence

ORD record
ord-51e9ef4e601840eabeeb99cdb14b040e
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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