Hydrochloric Acid → HCID 10780761, compound

HRID 2293702Notes

Reaction equation

HRID 2293702 reaction equation
[C:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=C(S(Cl)(=O)=O)C=CC=1.C([Li])CCC.[CH:34]1([CH:37]=[O:38])[CH2:36][CH2:35]1.Cl>O1CCCC1.CCCCCC.[Cl-].[Na+].O.C(OCC)(=O)C.O>[C:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:37]([CH:34]3[CH2:36][CH2:35]3)[OH:38])[CH:12]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 17943m-Bromobenzenesulphonyl chlorideHCID 123114CyclopropanecarboxaldehydeHCID 8190068HCID 8190068, compoundHCID 178418339Butyllithium2×

Product 1

HCID 10780761HCID 10780761, compoundYield 55%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 970 mg of N-phenyl-3-bromo-benzenesulfonamide, readily prepared from commercially available 3-bromo-benzene sulfonyl chloride, in 55 mL of anhydrous tetrahydrofuran under nitrogen at -78° C. is added 1.9 mL of a 1.6M solution of n-butyllithium in hexane. The solution is stirred for 10 min and then an additional 1.9 mL of n-butyllithium (1.6M in hexane) is added. The solution is stirred for 10 min and then 0.35 mL of cyclopropane carboxaldehyde is added. The solution is stirred for 1 h 30 min and then treated with water and ethyl acetate. The solution is treated with 5% aqueous hydrochloric acid and brine. The layers are separated and the aqueous is extracted with two portions of ethyl acetate. The combined organic layers are dried sodium sulfate (Na2SO4) and concentrated to afford an oil which is chromatographed over silica (eluted with 5% methanol/dichloromethane) to afford 517 mg (55%) of the title product as a clear oil.

Workup

  1. stirringThe solution is stirred for 10 min
  2. stirringThe solution is stirred for 1 h 30 min
  3. customThe layers are separated
  4. extractionthe aqueous is extracted with two portions of ethyl acetate
  5. concentrationconcentrated
  6. customto afford an oil which
  7. customis chromatographed over silica (eluted with 5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-d9644f44fdc943bba251084f17b46707
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

Loading…