Azobisisobutyronitrile → HCID 131718346, compound

HRID 486813Notes

Reaction equation

HRID 486813 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[C:6]([S:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[C:7]2=[O:12].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>CC(OC(C)=O)=O>[Br:20][CH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[CH:5]=[C:6]([S:13][CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[C:7]2=[O:12]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67851956HCID 67851956, compound

Product 1

HCID 131718346HCID 131718346, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The acid 1 (59 mmol), N-bromosuccinimide (59 mmol), and azobis (2-methyl-propionitrile) (0.5 g, 3 mmol) is combined in 200 mL of Ac2O and stirred at 120°-130° C. for about 0.5 hours. When the color lightens, the solution is poured onto ice. The yellow solid is collected and dissolved in CHCl3. The CHCl3 solution is dried using Na2SO4, concentrated to a small volume, and chromatographed on silica gel column (benzene) to yield the brominated acid (5-bromomethyl-1,4-naphthoquinonyl thio)-proprionic acid, designated as compound 1b.

Workup

  1. additionWhen the color lightens, the solution is poured onto ice
  2. customThe yellow solid is collected
  3. dissolutiondissolved in CHCl3
  4. dry with materialThe CHCl3 solution is dried
  5. concentrationconcentrated to a small volume
  6. customchromatographed on silica gel column (benzene)

Sources & evidence

ORD record
ord-794f053e9b5f471ea1e66446df3829ed
Source dataset
uspto-grants-1994_03
Patent number
US05292873

Reaction notes

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