Water → HCID 86690652, compound

HRID 1505619Notes

Reaction equation

HRID 1505619 reaction equation
[C:1]([NH:5][S:6]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1.O>CN(C)C(=O)C.CCOC(C)=O>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][N:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[S:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:8])=[O:7])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 562762N-tert-butyl-1-phenylmethanesulfonamide

Product 1

HCID 86690652HCID 86690652, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of N-tert-butyl-1-phenyl-methanesulfonamide (1 g, 4.39 mmol) in N,N-dimethylacetamide (15 mL) was added sodium hydride (60% in mineral oil) (211 mg, 5.3 mmol) and the reaction was stirred at ambient temperature for 30 minutes. 1-Bromo-4-(bromomethyl)benzene (1.21 g, 4.83 mmol) was then added and the reaction was stirred at 80° C. for 16 hours. Water was added and the reaction was diluted with EtOAc and washed with water (×2) and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-30% EtOAc in heptane) to give N-[(4-bromophenyl)methyl]-N-tert-butyl-1-phenyl-methanesulfonamide (1.18 g, 68% yield). LCMS (m/z) ES+ 397 [M+1]+.

Workup

  1. stirringthe reaction was stirred at 80° C. for 16 hours
  2. washwashed with water (×2) and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (0-30% EtOAc in heptane)

Sources & evidence

ORD record
ord-34139864a35b4dcb825f95dc83ca18d9
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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