Benzyl Bromide → HCID 4465336, compound

HRID 352394Notes

Reaction equation

HRID 352394 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>CN(C=O)C.O>[OH:1][CH2:2][CH2:3][N:4]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 22711621HCID 22711621, compound

Product 1

HCID 4465336HCID 4465336, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of 15.11 g (55 mmol) of N-(2-hydroxyethyl)-4-(n-butoxy)benzenesulfonamide from Example 2 in 100 mL of anhydrous DMF, was added 22.9 g (165 mmol) of powdered potassium carbonate and then 10.3 g (60 mmol) of benzyl bromide. After 16 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 20.7 g of crude product. This was recrystallized from ethyl acetate/hexane to afford 13.8 g of the desired N-(hydroxyethyl)-N-(phenylmethyl)-4-(n-butoxy)benzenesulfonamide.

Workup

  1. customthe organic layer separated
  2. washwashed 3×
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customto afford 20.7 g of crude product
  6. customThis was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-409c7f6be4054dd8888e9bce112c91c8
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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