Sodium hydride → HCID 54071394, compound

HRID 1383878Notes

Reaction equation

HRID 1383878 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].Br[CH2:9][C:10]1[C:11]([CH2:16]Br)=[CH:12][CH:13]=[CH:14][CH:15]=1>CN(C)C=O>[CH3:3][S:4]([N:7]1[CH:16]=[C:11]2[C:10]([CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:9]1)(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzeneHCID 72879Methanesulfonamide

Product 1

HCID 54071394HCID 54071394, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

Sodium hydride (0.88 g) was suspended in 3 ml dimethyl formamide. To this stirred solution was added methanesulfonamide (0.95 g, 10 mmol) in 5 ml dimethyl formamide dropwise under nitrogen. After stirring at 60° C. for 0.5 hours, a solution of 2.64 g (10 mmol) α,α′-dibromo-o-xylene in 7 ml DMF was added at a rate appropriate to maintain the temperature at 60-70° C. The mixture was stirred at room temperature for another hour, then quenched by pouring into water. The resulting precipitate was collected and washed with water, petroleum ether and ether successively. Weight 1.57 g (80%). 1H-NMR δ2.37 (s, 3H, —CH3), 4.709 (s, 4H, 2CH2). 7.25˜7.35 (m. 4H, ArH).

Workup

  1. temperatureto maintain the temperature at 60-70° C
  2. stirringThe mixture was stirred at room temperature for another hour
  3. customquenched
  4. additionby pouring into water
  5. customThe resulting precipitate was collected
  6. washwashed with water, petroleum ether and ether successively

Sources & evidence

ORD record
ord-53a9d89023084b609c7245862e8f3708
Source dataset
uspto-grants-2001_07
Patent number
US06255490B1

Reaction notes

Loading…