Toluene → HCID 19438761, compound

HRID 1733891Notes

Reaction equation

HRID 1733891 reaction equation
[C:1]([Cl:4])(Cl)=O.[C:5]1([CH3:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([N:19]1[C:28]2[C:23](=[CH:24][C:25]([N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=2)[NH:22]C(=O)[C:20]1=[O:39])C1C=CC=CC=1.C(=O)([O-])[OH:41].[Na+]>CN(C)C=O.O>[CH2:11]([O:41][N:19]1[C:28]2[C:23](=[CH:24][C:25]([N:33]3[CH:37]=[CH:36][N:35]=[CH:34]3)=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=2)[N:22]=[C:1]([Cl:4])[C:20]1=[O:39])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 19438770HCID 19438770, compound

Product 1

HCID 19438761HCID 19438761, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 20% phosgene in toluene (50 ml, 96 mmol) was added dropwise to a stirred solution of 12.1 g (30 mmol) of 1-benzyl-6-(1H-imidazol-1-yl)-7-trifluoromethylquinoxaline-2,3(1H,4H)-dione in 100 ml of dry N,N-dimethylformamide at room temperature. The mixture was stirred at room temperature overnight and neutralized by cautious addition of 16 g (190 mmol) of sodium hydrogen carbonate. After 10 min. the mixture was poured into 500 ml of water. Light petroleum (200 ml) was added under vigorous stirring and the solid formed was isolated by filtration. The product was washed with water and ether and dried in vacuo to give 11.0 g (87%) of crude title compound.

Workup

  1. customthe solid formed
  2. customwas isolated by filtration
  3. washThe product was washed with water and ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9202cccd3fb647e1844da6fab3cba3f8
Source dataset
uspto-grants-1996_07
Patent number
US05532236

Reaction notes

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