Phosphorus tribromide → HCID 20222405, compound

HRID 980307Notes

Reaction equation

HRID 980307 reaction equation
P(Br)(Br)[Br:2].O[CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=2)[NH:10][CH:9]=1>C1COCC1.O>[Br:2][CH2:6][CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[CH:15]=2)[NH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 20222397HCID 20222397, compound

Product 1

HCID 20222405HCID 20222405, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Phosphorus tribromide (0.03 ml) was added dropwise to a solution of N-[[3-(2-hydroxyethyl)-1H-indol-5-yl]methyl]methanesulphonamide (0.18 g) in dry THF (20 ml) stirred in an ice bath. There was an immediate reddish colour produced. The solution was stirred for 2 h and then at room temperature for a further 3.5 h, then again chilled in ice, diluted with water (40 ml) and extracted with ether (2×50 ml, 3×25 ml) combined extracts were washed with brine (3×20 ml) and dried (Na2SO4). Removal of the solvent by rotary evaporation at 35°-40° afforded the title compound as a viscous pink oil (0.22 g).

Workup

  1. customproduced
  2. stirringThe solution was stirred for 2 h
  3. temperatureagain chilled in ice
  4. extractionextracted with ether (2×50 ml, 3×25 ml)
  5. washwere washed with brine (3×20 ml)
  6. dry with materialdried (Na2SO4)
  7. customRemoval of the solvent
  8. customby rotary evaporation at 35°-40°

Sources & evidence

ORD record
ord-84da0199b34e4b66bfab1d444ae72841
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

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