Formamide → HCID 86639522, compound

HRID 1022399Notes

Reaction equation

HRID 1022399 reaction equation
[CH:1]([NH2:3])=[O:2].[H-].[Na+].Cl[C:7]1[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:23])[CH:13]=2)[N:8]=1.O>CN(C=O)C>[Cl:23][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:3][CH:1]=[O:2])[N:16]=[C:15]2[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 713FormamideHCID 962WaterHCID 24758Sodium hydrideHCID 16282212,6-dichloro-4-phenylquinazoline

Product 1

HCID 86639522HCID 86639522, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 54 mg of dry formamide in DMF (5 ml) was added 48 mg of sodium hydride (60%), followed by stirring at room temperature for 30 minutes. To the reaction mixture was added 275 mg of 2,6-dichloro-4-phenylquinazoline (compound No. Ia1-3), followed by warming to 85° C. and further stirring for 3 hours. The resulting reaction solution was poured into 100 ml of water and extracted with ethyl acetate. The extract was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain 64 mg of the titled compound. Mp.252.1° C. 1H NMR: 7.59-7.66 (3H, m), 7.72-7.81 (3H, m), 7.88 (1H, d, J=8.8 Hz), 8.02 (1H, d, J=2.0 Hz), 8.37 (1H, br. d, J=10.4 Hz), 9.71 (1H, d, J=10.4 Hz).

Workup

  1. temperatureby warming to 85° C.
  2. stirringfurther stirring for 3 hours
  3. customThe resulting reaction solution
  4. extractionextracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-123331fd33d1444195bd83ea4cc0fd61
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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