Formamide → HCID 135744166, compound

HRID 2233245Notes

Reaction equation

HRID 2233245 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-0e2301f94806407faff8fdb3f744b6a4
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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