Azobisisobutyronitrile → HCID 13827091, compound

HRID 1252731Notes

Reaction equation

HRID 1252731 reaction equation
[CH2:1]([O:3][C:4]1[O:9][C:8](=[O:10])[C:7]2[C:11]([CH3:15])=[CH:12][CH:13]=[CH:14][C:6]=2[N:5]=1)[CH3:2].[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>>[Br:16][CH2:15][C:11]1[C:7]2[C:8](=[O:10])[O:9][C:4]([O:3][CH2:1][CH3:2])=[N:5][C:6]=2[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 504661HCID 504661, compound

Product 1

HCID 13827091HCID 13827091, compound

Procedure

A solution of 2-ethoxy-5-methyl-4H-3,1-benzoxazin-4-one (330 mg), N-bromosuccinimide (340 mg) and AIBN (10 mg, 2,2'-azobis-iso-butyronitrile) was refluxed for 21/2 hours. The solution was evaporated to dryness. The residue was purified by column chromatography (silica gel) 10% ethyl acetate:petroleum ether 30-60). This afforded the title compound, 5-bromomethyl-2-ethoxy-4H-3,1-benzoxazin-4-one, m.p. 112°-114° C.; IR: 1760, 1630, 1590 cm-1.

Workup

  1. customThe solution was evaporated to dryness
  2. customThe residue was purified by column chromatography (silica gel) 10% ethyl acetate

Sources & evidence

ORD record
ord-660518900a014aaaa98ca2bca29d01eb
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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