1,2-Dibromoethane → HCID 86676883, compound

HRID 1854524Notes

Reaction equation

HRID 1854524 reaction equation
[C:1](O[K])([CH3:4])(C)C.[N+:7]([C:10]1[N:11]=[CH:12][NH:13][CH:14]=1)([O-:9])=[O:8].Br[CH2:16][CH2:17]Br>CN(C=O)C>[N+:7]([C:10]1[N:11]=[CH:12][N:13]([CH2:16][CH2:17][N:11]2[CH:4]=[C:1]([N+:7]([O-:9])=[O:8])[N:13]=[CH:12]2)[CH:14]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 178418922HCID 178418922, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 86676883HCID 86676883, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

tBuOK (5 g, 44 mmol) was added in portions to a suspension of 4-nitroimidazole in anhydrous DMF (100 mL) at 0° C., then the reaction mixture was stirred at r. t. for 3 h, a solution of 1,2-dibromoethane in anhydrous DMF (20 mL) was added into the above mixture. The reaction solution was stirred at r. t. for 3 days, and was poured into ice-water (200 mL) for standing up for 2 h, then filtered. The filtered cake was washed with EtOH/CH2Cl2 (1/1) and dried to provide 64 (2.3 g, 45%) as off-white solid, which was pure enough to be used next step.

Workup

  1. stirringThe reaction solution was stirred at r
  2. waitfor 3 days
  3. waitfor standing up for 2 h
  4. filtrationfiltered
  5. washThe filtered cake was washed with EtOH/CH2Cl2 (1/1)
  6. customdried

Sources & evidence

ORD record
ord-b4cbc78b74c8423eb977964375862d29
Source dataset
uspto-grants-2015_02
Patent number
US08962670B2

Reaction notes

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