Water → HCID 86721863, compound

HRID 1049002Notes

Reaction equation

HRID 1049002 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:27][CH:28]([CH3:30])[CH3:29].O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:10])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 86721862HCID 86721862, compound

Product 1

HCID 86721863HCID 86721863, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-methanesulfonamide (0.61 g, 1.68 mmol) and K2CO3 (464 mg, 3.4 mmol) in dimethylformamide (5 mL) was added 1-iodo-2-methylpropane (584 μL, 5.0 mmol). The mixture was heated at 100° C. in microwave reactor for 3 hours. Water was added and the reaction extracted with EtOAc, washed with brine, dried with Na2SO4, concentrated and purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give C-(4-bromo-phenyl)-N-(3-chloro-phenyl)-N-isobutyl-methanesulfonamide (423 mg, 1.0 mmol, 60%). LCMS (m/z, Method A) ES+ 415.8 [M+1]+.

Workup

  1. extractionthe reaction extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (0-50% DCM in cyclohexane)

Sources & evidence

ORD record
ord-0e8e30cc81764cc587e6da1b8a66dd8f
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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