Dimethylformamide → 1-(2-Chlorophenyl)-3,4-dimethyl-7-(3-nitrobenzyloxy)-imidazo(1,5-a)quinoxaline

HRID 254317Notes

Reaction equation

HRID 254317 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[C:13]3[C:18]([N:19]=[C:20]([CH3:21])[C:11]2=[C:10]([CH3:23])[N:9]=1)=[CH:17][C:16]([OH:22])=[CH:15][CH:14]=3.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[N+:35]([C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH2:41]Br)([O-:37])=[O:36]>O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[C:13]3[C:18]([N:19]=[C:20]([CH3:21])[C:11]2=[C:10]([CH3:23])[N:9]=1)=[CH:17][C:16]([O:22][CH2:41][C:40]1[CH:43]=[CH:44][CH:45]=[C:38]([N+:35]([O-:37])=[O:36])[CH:39]=1)=[CH:15][CH:14]=3

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 42629710HCID 42629710, compound

Product 1

HCID 426298301-(2-Chlorophenyl)-3,4-dimethyl-7-(3-nitrobenzyloxy)-imidazo(1,5-a)quinoxaline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
120 °C

Procedure

1.5 g 1-(2-Chloro-phenyl)-3,4-dimethyl-7-hydroxy-imidazo(1,5-a)quinoxaline, 3.36 g Caesium carbonate, 80 mL N,N-dimethylformamide, and 9 mL water were stirred for 10 min followed by addition of 1.3 g 3-nitro-benzylbromide. After 3 h stirring at 120° C. the reaction mixture was given into 250 mL water, filtered off, washed with water, dried under reduced pressure.

Workup

  1. filtrationfiltered off
  2. washwashed with water
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-44a65d42130c4c5c9da490663afcfc22
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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