Water → HCID 86690647, compound

HRID 1505614Notes

Reaction equation

HRID 1505614 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:12])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:23][CH:24]([CH3:26])[CH3:25].O>CN(C)C(=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 61401001HCID 61401001, compound

Product 1

HCID 86690647HCID 86690647, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-[(4-bromophenyl)methyl]-1-phenyl-methanesulfonamide (Example 5, Step 1) (2 g, 5.82 mmol) in N,N-dimethylacetamide (20 mL) was added sodium hydride (60% in mineral oil) (353 mg, 8.8 mmol) and the reaction was stirred at ambient temperature for 30 minutes. 1-Bromo-2-methyl-propane (0.96 mL, 8.81 mmol) was then added and the reaction was stirred for 16 hours. Water was added and the reaction was diluted with EtOAc. The reaction was then washed with water (3×) and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-50% EtOAc in heptane) to give N-[(4-bromophenyl)methyl]-N-isobutyl-1-phenyl-methanesulfonamide (1.20 g, 52% yield). LCMS (m/z) ES+ 418.1 [M+Na]+.

Workup

  1. stirringthe reaction was stirred for 16 hours
  2. washThe reaction was then washed with water (3×) and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (0-50% EtOAc in heptane)

Sources & evidence

ORD record
ord-51d62e937048436aa9ddff2ffad6edb1
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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