N-bromobutanimide → HCID 20296689, compound

HRID 1091780Notes

Reaction equation

HRID 1091780 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:11].N(/C(C)(C)C#N)=N\C(C)(C)C#N.[Br:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:24][CH:4]1[C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[Cl:1])[C:6](=[O:11])[O:5]1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 30403001(3H)-Isobenzofuranone, 4-chloro-HCID 178449902HCID 178449902, compound

Product 1

HCID 20296689HCID 20296689, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-chloroisobenzofuran-1(3H)-one (10 g, 59.32 mmol), (E)-2,2′-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.974 g, 5.93 mmol) and 1-bromopyrrolidine-2,5-dione (11.61 g, 65.25 mmol) were dissolved CCl4 (100 mL) and heated at reflux for 2 hours. The reaction was cooled and filtered, the filtrate was evaporated to the desired compound as a yellow gum (14.20 g, 97% yield); 1H NMR (400.132 MHz, CDCl3) δ 7.32 (1H, s), 7.61 (1H, t), 7.73 (1H, d), 7.88 (1H, d); m/z (LC-MS, ESI+), RT=2.28 (M+H not detected).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-a8e037c0e6624cec8cddb1a406e82aae
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

Loading…