Bromine → HCID 22482331, compound

HRID 2181801Notes

Reaction equation

HRID 2181801 reaction equation
[CH2:1]([CH:3]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH3:2].[Br:28]Br>ClCCl>[Br:28][C:8]1[CH:7]=[CH:6][C:5]2[N:4]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)(=[O:18])=[O:19])[CH:3]([CH2:1][CH3:2])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 22482377HCID 22482377, compound

Product 1

HCID 22482331HCID 22482331, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 6-ethyl-5-[(4-methoxyphenyl)sulfonyl]-5,6-dihydrophenanthridine (6.0 g, 15.8 mmol) in dichloromethane (800 mL) was treated drop-wise with excess bromine (2.1 mL, 41 mmol). The reaction mixture was heated to reflux and additional bromine (1.0 mL, 10 mmol) was added. The reaction was cooled and stirred at room temperature overnight. The reaction mixture was washed sequentially with a saturated, aqueous sodium thiosulfate solution, water, and a saturated, aqueous, sodium chloride solution. The organic phase was dried over anhydrous magnesium sulfate, filtered through a short column of silica gel, and the solvent was removed in vacuo to afford a crude yellow solid. The crude solid was crystallized from a mixture of ethyl acetate-hexane (1:1), and yielded the title compound (6.3 g, 13.8 mmol, 87%) as a colorless, crystalline solid;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction was cooled
  4. washThe reaction mixture was washed sequentially with a saturated, aqueous sodium thiosulfate solution, water
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered through a short column of silica gel
  7. customthe solvent was removed in vacuo
  8. customto afford a crude yellow solid
  9. customThe crude solid was crystallized from a mixture of ethyl acetate-hexane (1:1)

Sources & evidence

ORD record
ord-5751b7a105ad4056bd140879d157652c
Source dataset
uspto-grants-2005_05
Patent number
US06894061B2

Reaction notes

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