Formamide → 6-(1-Imidazolyl)-3,4-dihydroquinazolin-4-one

HRID 618669Notes

Reaction equation

HRID 618669 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][N:13]=[CH:12]2)=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH:16](N)=O>O>[N:11]1([C:8]2[CH:7]=[C:3]3[C:2](=[CH:10][CH:9]=2)[N:1]=[CH:16][NH:6][C:4]3=[O:5])[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 713FormamideHCID 218478212-Amino-5-(1-imidazolyl)benzamide

Product 1

HCID 1358228196-(1-Imidazolyl)-3,4-dihydroquinazolin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 2-amino-5-(1-imidazolyl)benzamide (12.0 g) and formamide (30 ml) was heated at 160° C. for 3 hours. The mixture was cooled and added to water. The precipitate was filtered off and washed with water to give 6-(1-imidazolyl)-3,4-dihydroquinazolin-4-one (7.5 g); NMR Spectrum: (CD3SOCD3) 7.15 (s, 1H), 7.80 (s, 1H), 7.90 (s, 1H), 8.13 (m, 2H), 8.26 (d, 1H), 8.41 (s, 1H);

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe precipitate was filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-f235411db01f446583668876f74e15be
Source dataset
uspto-grants-1999_09
Patent number
US05955464

Reaction notes

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