N-bromobutanimide → HCID 19759379, compound

HRID 248366Notes

Reaction equation

HRID 248366 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[CH:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[C:3]=1[C:15]#[N:16].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:17][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([N:4]2[CH:5]=[C:6]([Cl:7])[C:2]([Cl:1])=[C:3]2[C:15]#[N:16])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 19759250HCID 19759250, compound

Product 1

HCID 19759379HCID 19759379, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3,4-dichloro-1-(4-methylphenyl)pyrrole-2-carbonitrile (1.25 g), 2,2'-azobisisobutyronitrile (10 mg) and N-bromosuccinimide (1.068 g) in carbon tetrachloride (25 ml) was refluxed for 3 hours, cooled to ambient temperature, and filtered. The filtrate was concentrated in vacuo. The residue was crystallized from 10% ethyl acetate in n-hexane to yield 1-(4-bromomethylphenyl)-3,4-dichloropyrrole-2-carbonitrile (1.01 g).

Workup

  1. temperaturewas refluxed for 3 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was crystallized from 10% ethyl acetate in n-hexane

Sources & evidence

ORD record
ord-7665858eb0dc427f97697edf14764448
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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