2-Amino-5-nitrobenzophenone → 4-Phenyl-6-nitro-quinazoline

HRID 919176Notes

Reaction equation

HRID 919176 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[NH2:19][C:20](N)=S>CS(C)=O>[C:6]1([C:4]2[C:3]3[C:2](=[CH:15][CH:14]=[C:13]([N+:16]([O-:18])=[O:17])[CH:12]=3)[N:1]=[CH:20][N:19]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 156812-Amino-5-nitrobenzophenoneHCID 2723790Thiourea

Product 1

HCID 142028674-Phenyl-6-nitro-quinazolineYield 39.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a 20 mL microwave reaction vial with a micro magnetic stir bar, were added 0.297 g of 2-amino-5-nitrobenzophenone, 0.186 g of thiourea and 3.0 mL of DMSO. Then the vial was sealed and heated with microwave at 140° C. for 20 hours. Two layers of liquid formed with brown liquid on the top and a dark brown gel like layer at the bottom. The reaction mixture was extracted with EtOAc and purified on column chromatography using hexane/EtOAc (5:1 to 4:1) as eluent, and 0.122 g of 4-phenyl-6-nitro-quinazoline was obtained, in a yield of 39.7%.

Workup

  1. customTo a 20 mL microwave reaction vial with a micro magnetic stir bar
  2. customThen the vial was sealed
  3. customTwo layers of liquid formed with brown liquid on the top
  4. extractionThe reaction mixture was extracted with EtOAc
  5. custompurified on column chromatography

Sources & evidence

ORD record
ord-59ddccb812964018a0a9e81210fdb4bd
Source dataset
uspto-grants-2016_03
Patent number
US09273012B2

Reaction notes

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