Benzamide → HCID 68717214, compound

HRID 2353445Notes

Reaction equation

HRID 2353445 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:13][C:14]1[C:18]([CH2:19]Cl)=[CH:17][O:16][CH:15]=1>CN(C)C=O>[C:1]([N:9]1[CH2:13][C:14]2=[CH:15][O:16][CH:17]=[C:18]2[CH2:19]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2331BenzamideHCID 24758Sodium hydrideHCID 127555563,4-Bis(chloromethyl)furan

Product 1

HCID 68717214HCID 68717214, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzamide (1.38 g) in N,N-dimethylformamide (40 mL) at 0° C., sodium hydride (1.37 g, 60%) was added. The mixture was stirred at ambient temperature for 10 min followed by addition of 3,4-bis(chloromethyl)furan (1.88 g). The resulting mixture was stirred for two days, diluted with ice-water (50 mL) and extracted with ethyl acetate (3×20 mL). The combine organic layers were dried over anhydrous sodium sulfate, filtered and evaporated and purified on a Biotage Horizon® system (silica, ethyl acetate/hexane 40/60) to yield the title compound.

Workup

  1. stirringThe resulting mixture was stirred for two days
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combine organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on a Biotage Horizon® system (silica, ethyl acetate/hexane 40/60)

Sources & evidence

ORD record
ord-6c24a6a7b664429fb9252681681c70ff
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

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