1-Bromopentane → HCID 57152813, compound

HRID 352391Notes

Reaction equation

HRID 352391 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+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(OCC)(=O)C>CN(C=O)C.O>[OH:1][CH2:2][CH2:3][N:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[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 80571-BromopentaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2055080HCID 2055080, compound

Product 1

HCID 57152813HCID 57152813, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Part A: To a solution of 2.0 g (8.6 mmol) of N-(2-hydroxyethyl)-4-methoxybenzenesulfonamide from Example 1 in 20 mL of anhydrous DMF, was added 3.58 g (25.9 mmol) of powdered potassium carbonate and then 1.96 g (13 mmol) of 1-bromopentane. 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 2.3 g of crude product. This was chromatographed on 150 g of silica gel using 20%-50% ethyl acetate/hexane to afford 2.12 g of the desired N-(hydroxyethyl)-N-pentyl-4-methoxybenzenesulfonamide, m/e=302 (M+H).

Workup

  1. customthe organic layer separated
  2. washwashed 3×
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customto afford 2.3 g of crude product
  6. customThis was chromatographed on 150 g of silica gel using 20%-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-8c05f3df352247adbc8bd934e34215e3
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

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