Azobisisobutyronitrile → HCID 58877917, compound

HRID 600210Notes

Reaction equation

HRID 600210 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]([N:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[CH3:21])(=[O:13])=[O:12])[CH2:7][CH2:6]1)=[O:4].C1C(=O)N([Br:31])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[S:11]([N:8]1[CH2:7][CH2:6][N:5]([C:3](=[O:4])[C:2]([F:1])([F:22])[F:23])[CH2:10][CH2:9]1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58877924HCID 58877924, compound

Product 1

HCID 58877917HCID 58877917, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of Intermediate 2 (37.5 g, 105.9 mmol), NBS (19.4 g, 105.9 mmol) and AIBN (0.45 g, 2.8 mmol) in carbon tetrachloride (500 mL) was refluxed for 4 h. The mixture was cooled, concentrated and purified over silica gel eluting with EtOAc to give the title compound contaminated with starting material and dibrominated side-product as amber oil (41.0 g). LCMS (M+H) calcd for C13H14F4N2O3SBr: 433.97; found: 433.01.

Workup

  1. temperaturewas refluxed for 4 h
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated
  4. custompurified over silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-29c07f4ceeb44a648410c2a5af1aa93b
Source dataset
uspto-grants-2011_03
Patent number
US07902182B2

Reaction notes

Loading…