Diethyl Ether → HCID 18928139, compound

HRID 1893433Notes

Reaction equation

HRID 1893433 reaction equation
[N:1]1([C:6]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:7]=2[NH2:8])[CH:5]=[CH:4][N:3]=[CH:2]1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[O:18].C(OCC)C>ClC1C=CC=CC=1Cl>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:9]=[C:7]2[C:6](=[CH:12][CH:11]=1)[N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:17](=[O:18])[NH:8]2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 48004302-(1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Product 1

HCID 18928139HCID 18928139, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a solution of 2-(1H-imidazol-1-yl)-5-(trifluoromethyl)aniline (17.00 g; 74.8 mmol; 1 eq) in anhydrous 1,2-dichlorobenzene (375 mL), commercially available carbonyldiimidazole (24.72 g; 149.7 mmol; 2 eq) is added under an argon atmosphere. This reaction mixture is allowed to stir under reflux for 2 hours. The expected quinoxalinone precipitates as a grey powder during the reflux. The initial crystal clear solution quickly turns black after heating and becomes non homogeneous. This crude reaction mixture is allowed to precipitate at 4° C. during 48 hours. The grey powder formed is then filtered off on a fritted glass. This solid is transferred in a 1 L flask, diluted in fresh ethyl acetate (500 mL) and heated to gentle reflux for two hours. Hot filtration and then several washings of the solid with diethyl ether afforded the title compound (14.28 g; 56.4 mmol; 75%) as a grey powder.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe expected quinoxalinone precipitates as a grey powder during the reflux
  3. temperatureThe initial crystal clear solution quickly turns black after heating
  4. customThis crude reaction mixture
  5. customto precipitate at 4° C. during 48 hours
  6. customThe grey powder formed
  7. filtrationis then filtered off on a fritted glass
  8. customThis solid is transferred in a 1 L flask
  9. additiondiluted in fresh ethyl acetate (500 mL)
  10. temperatureheated
  11. temperatureto gentle reflux for two hours
  12. filtrationHot filtration

Sources & evidence

ORD record
ord-4ec2e3e26a0f465299bcca713ee5d287
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…