N-bromobutanimide → HCID 59333304, compound

HRID 1893472Notes

Reaction equation

HRID 1893472 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([CH:17]=[CH:18][N:19]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:7][CH:6]=2.[Br:20]N1C(=O)CCC1=O>ClCCl>[Br:20][C:17]1[N:4]2[C:5]3[C:10]([N:11]=[C:2]([Cl:1])[C:3]2=[N:19][CH:18]=1)=[CH:9][C:8]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:7][CH:6]=3

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59333325HCID 59333325, compound

Product 1

HCID 59333304HCID 59333304, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred solution of 4-chloro-7-(trifluoromethoxy)imidazo[1,2-a]quinoxaline (5.4 g, 18.8 mmol, 1 eq) prepared as described in example 7 step 4 in dichloromethane (94 mL) is added N-bromosuccinimide (5.0 g; 28.2 mmol; 1.5 eq). The solution becomes green during the addition. The solution is allowed to stir for 7 hours at 30° C. until completion of the reaction. Then, the solution is concentrated under vacuum and purified by chromatography on a silica gel column (chloroform/cyclohexane 7:3) to afford the title compound still contaminated by 10% of residual N-bromosuccinimide (7.2 g; 17.7 mmol; 94%). The compound is used as such in the next step without further purification.

Workup

  1. additionThe solution becomes green during the addition
  2. concentrationThen, the solution is concentrated under vacuum
  3. custompurified by chromatography on a silica gel column (chloroform/cyclohexane 7:3)

Sources & evidence

ORD record
ord-c8d2f511c5f64d0ba2b5f91592e61055
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…