Water → HCID 57437661, compound

HRID 1618467Notes

Reaction equation

HRID 1618467 reaction equation
[N:1]1([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Br:18]N1C(=O)CCC1=O.O>O1CCOCC1>[Br:18][C:2]1[N:1]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 5328435SBB025753

Product 1

HCID 57437661HCID 57437661, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 1 (25.75 grams, 117.5 mmol) was dissolved in dioxane (400 mL). To this was added N-bromosuccinimide (20.91 grams, 117.5 mmol). This was stirred at reflux for 3 hours after which time the mixture was poured into water and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated in vacuo and chromatographed (silica gel) using a mobile phase of dichloromethane-ethyl acetate 5:1 (v/v) to provide the title compound. Mass spectral and NMR data confirm the structure. Also synthesized analogously was the 5,6-dimethylbenzimidazole analog.

Workup

  1. temperatureat reflux for 3 hours after which time the mixture
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customchromatographed (silica gel)

Sources & evidence

ORD record
ord-a5860304a7d1445c9d9a5ee5d4f33e55
Source dataset
uspto-grants-2014_07
Patent number
US08766529B2

Reaction notes

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