Formamide → HCID 135744166, compound

HRID 2213867Notes

Reaction equation

HRID 2213867 reaction equation
[NH2:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:10]([O:19][CH3:20])=[CH:9][C:3]=1[C:4](OCC)=[O:5].[CH:21]([NH2:23])=O>C(O)C>[CH3:20][O:19][C:10]1[CH:9]=[C:3]2[C:2](=[CH:12][C:11]=1[O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:1]=[CH:21][NH:23][C:4]2=[O:5]

Participants

4

Reactant 2

HCID 713FormamideHCID 21958889HCID 21958889, compound

Product 1

HCID 135744166HCID 135744166, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of ethyl 2-amino-4-(2,2,2-trifluoroethoxy)-5-methoxybenzoate (20.2 g, 69.1 mmol) and formamide (50 ml) was heated at 175° C. for 6 hours. The mixture was allowed to cool to ambient temperature, ethanol (150 ml) was added and the reaction allowed to stand for 18 hours. Collection of the solid which had precipitated by suction filtration, followed by washing with ethanol (2×50 ml) and drying in vacuo, yielded 6-methoxy-7-(2,2,2-trifluoroethoxy)-3,4-dihydroquinazolin-4-one (15.8 g, 84% yield) as a pale brown crystalline solid:

Workup

  1. temperatureto cool to ambient temperature
  2. customCollection of the solid which
  3. customhad precipitated by suction filtration
  4. washby washing with ethanol (2×50 ml)
  5. customdrying in vacuo

Sources & evidence

ORD record
ord-d5f7b9aa071949d682352e559006b74b
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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