Boron Trichloride → HCID 58896047, compound

HRID 269438Notes

Reaction equation

HRID 269438 reaction equation
B(Cl)(Cl)Cl.C[O:6][C:7]1[CH:8]=[C:9]([N:15]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:10]=[C:11]([O:13]C)[CH:12]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[OH:6][C:7]1[CH:8]=[C:9]([N:15]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:10]=[C:11]([OH:13])[CH:12]=1

Participants

5

Reactant 2

HCID 25135Boron TrichlorideHCID 58896084HCID 58896084, compound

Product 1

HCID 58896047HCID 58896047, compoundYield 286.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Boron trichloride solution (145 mL, 1.0 M in CH2Cl2) was added dropwise to a solution of N-(3,5-Dimethoxy-phenyl)-N-heptyl-4-methyl-benzenesulfonamide (19.0 g, 47 mmol) and tetrabutylammonium iodide (53.5 g, 145 mmol) in 250 mL of anhydrous dichloromethane at −78° C. under argon atmosphere. The reaction mixture was stirred at −78° C. for 20 minutes, and then at 0° C. for 2 h. The reaction was quenched by addition of 100 mL of water slowly. The organic layer was separated and washed with water, 30% aqueous NaHSO3 solution, water and brine, and dried over anhydrous sodium sulfate. Removal of solvent and drying reagent provided 50.83 g of a semi-solid crude product. This material was chromatographed on silica gel column eluted with a mixture of petroleum ether and acetone (2:1) to afford 16.83 g (94.6%) of the title compound as a light yellow solid.

Workup

  1. waitat 0° C. for 2 h
  2. customThe reaction was quenched by addition of 100 mL of water slowly
  3. customThe organic layer was separated
  4. washwashed with water, 30% aqueous NaHSO3 solution, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of solvent
  7. customdrying reagent

Sources & evidence

ORD record
ord-a174ec7e9aa04a139af4b3c5f5a29bed
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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