Azobisisobutyronitrile → HCID 59341197, compound

HRID 15012Notes

Reaction equation

HRID 15012 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH2:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH2:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59341184HCID 59341184, compound

Product 1

HCID 59341197HCID 59341197, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a solution of 2.16 gm (9.0 mmol) of acetic acid 2-(6-methyl-2-nitro-pyridin-3-yloxy)-ethyl ester 94, 1.76 gm (9.9 mmol) of N-bromosuccinimide in 125 mL of CCl4 was added 0.074 gm (44.9 μmol) of AIBN and the reaction was heated to reflux for 1 h. After 1 h a 500 watt sun lamp was used to irradiate the refluxing solution for an additional 4 h. The mixture was poured into 300 mL of CCl4 and washed with water twice (150 mL), saturated brine and the organic layer was dried (anhydrous Na2SO4) and the solvents removed at reduced pressure. Column chromatography of the residue using 50%-30%-10% CH2Cl2-hexanes yielded 1.06 gm (37%) of a light yellow solid. 1H NMR (400 MHz, CDCl3) δ: 2.06 (s, 3H), 4.31 (t, 2H, J=4.1 Hz), 4.41 (t, 2H, J=4.1 Hz), 4.48 (s, 2H), 7.49 (d, 2H, J=8.5 Hz), 7.65 (d, 2H J=8.5 Hz).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 1 h
  3. customto irradiate the refluxing solution for an additional 4 h
  4. washwashed with water twice (150 mL), saturated brine
  5. dry with materialthe organic layer was dried (anhydrous Na2SO4)
  6. customthe solvents removed at reduced pressure

Sources & evidence

ORD record
ord-359526b6852f4781ab725ae931f3151d
Source dataset
uspto-grants-2010_06
Patent number
US07732457B2

Reaction notes

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