Triphenylphosphine → HCID 21842622, compound

HRID 1737448Notes

Reaction equation

HRID 1737448 reaction equation
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]([CH2:42][CH2:43][CH2:44]O)[CH2:30][N:31]([CH3:41])[S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)(=[O:34])=[O:33])[CH:26]=[CH:27][CH:28]=1>C(#N)C>[Br:1][CH2:44][CH2:43][CH2:42][CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[CH2:30][N:31]([CH3:41])[S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 21842614N-(2-(3-Chlorophenyl)-5-hydroxypentyl)-N-methylbenzenesulfonamide

Product 1

HCID 21842622HCID 21842622, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Bromine was added to a solution of triphenylphosphine (41.4 mg, 0.158 mmol) in 0.50 mL of acetonitrile until the red color persisted, and a small additional quantity of triphenylphorsphine was then added to consume the excess bromine. A solution of N-(2-(3-chlorophenyl)-5-hydroxypentyl)-N-methylbenzenesulfonamide (38.7 mg, 0.105 mmol) in 0.3 mL of acetonitrile was added. After stirring for 1 h, the reaction was quenched by a solution of sodium sulfite (20 mg) dissolved in 1.0 mL of water. The mixture was diluted with 15 mL of sodium bicarbonate and extracted with 2×20 mL of ethyl acetate. The organic layers were washed with 15 mL of brine, dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography on silica gel, eluting with of 10% ethyl acetate in hexane to give 23 mg the title compound.

Workup

  1. additiona small additional quantity of triphenylphorsphine was then added
  2. customto consume the excess bromine
  3. customthe reaction was quenched by a solution of sodium sulfite (20 mg)
  4. dissolutiondissolved in 1.0 mL of water
  5. additionThe mixture was diluted with 15 mL of sodium bicarbonate
  6. extractionextracted with 2×20 mL of ethyl acetate
  7. washThe organic layers were washed with 15 mL of brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe crude product was purified by flash column chromatography on silica gel
  11. washeluting with of 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-240198b4a6924a729796830aac143154
Source dataset
uspto-grants-1999_10
Patent number
US05962462

Reaction notes

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