HCID 22049841, compound → HCID 22049843, compound

HRID 1830927Notes

Reaction equation

HRID 1830927 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[S:9]([CH2:12][C:13](=[O:15])[CH3:14])(=[O:11])=[O:10])=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[Br:29][Br-]Br>C(O)(=O)C.ClCCl.C(OCC)(=O)C>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[S:9]([CH2:12][C:13](=[O:15])[CH2:14][Br:29])(=[O:10])=[O:11])=[CH:21][CH:20]=1

Participants

5

Reactant 1

HCID 22049841HCID 22049841, compound

Product 1

HCID 22049843HCID 22049843, compoundYield 49.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-[bis-(4-chloro-phenyl)-methanesulfonyl]-propan-2-one (Example 1, 0.63 g, 1.7 mmol) in a mixture of 10 mL of acetic acid and 60 mL of dichloromethane was added pyridine hydrobromide perbromide (0.62 g, 1.9 mmol) using a procedure such as those described in Grossert J. S. et al., Can. J. Chem. 1984; 62:798. The reaction mixture was stirred at room temperature for 18 hours and then evaporated to give an oil. The oil was dissolved in 200 mL of ethyl acetate, washed with three 50 mL portions of 5% aqueous sodium bicarbonate and then with 50 mL of brine. The organic layer was separated, dried (sodium sulfate), filtered, and then evaporated to afford an oil, which was chromatographed (silica gel, eluting with 30% ethyl acetate in hexane) to give 0.37 g (48%) of a white solid with mp 122–123° C.; 1H NMR (deuterochloroform): δ 4.03 (s, 2H), 4.09 (s, 2H), 5.64 (s, 1H), 7.33–7.41 (m, 4H), 7.51–7.58 (m, 4H); ms: m/z 435 (m−1) APCI-.

Workup

  1. customevaporated
  2. customto give an oil
  3. washwashed with three 50 mL portions of 5% aqueous sodium bicarbonate
  4. customThe organic layer was separated
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. customevaporated
  8. customto afford an oil, which
  9. customwas chromatographed
  10. wash(silica gel, eluting with 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-0cd5bc4620ee4b708d64105dbadcb458
Source dataset
uspto-grants-2006_06
Patent number
US07067538B2

Reaction notes

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