Benzyl Bromide → HCID 563866, compound

HRID 352390Notes

Reaction equation

HRID 352390 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(OCC)(=O)C>CN(C=O)C.O>[OH:1][CH2:2][CH2:3][N:4]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2055080HCID 2055080, compound

Product 1

HCID 563866HCID 563866, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of 10.04 g (43 mmol) of N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide from Example 1 in 85 mL of anhydrous DMF, was added 17.8 g (128 mmol) of powdered potassium carbonate and then 8.2 g (48 mmol) of benzyl bromide. After 24 hours, ethyl acetate and water was added, the organic layer separated and washed 3×s with brine, dried with sodium sulfate, filtered and stripped to afford 14.3 g of crude product. This was recrystallized from tert-butylmethyl ether/hexane to afford 9.0 g of the desired N-(hydroxyethyl)-N-(phenylmethyl)-4-methoxybenzenesulfonamide.

Workup

  1. customthe organic layer separated
  2. washwashed 3×
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customto afford 14.3 g of crude product
  6. customThis was recrystallized from tert-butylmethyl ether/hexane

Sources & evidence

ORD record
ord-837731fb76a344179840f1ae375ef120
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

Loading…