Formamide → 6,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

HRID 1797886Notes

Reaction equation

HRID 1797886 reaction equation
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH3:19])[C:12]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:11][C:6]=1[C:7](OC)=[O:8]>CN1CCCC1=O>[CH3:24][O:23][CH2:22][CH2:21][O:20][C:12]1[CH:11]=[C:6]2[C:5](=[CH:14][C:13]=1[O:15][CH2:16][CH2:17][O:18][CH3:19])[N:4]=[CH:1][NH:3][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 713FormamideHCID 66524239HCID 66524239, compound

Product 1

HCID 1354093056,7-Bis(2-methoxyethoxy)quinazolin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
167.5 °C

Procedure

Formamide (130 mL) was added to a solution of compound 21 (13.0 g, 43.43 mmol) in N-methyl-2-pyrrolidone (130 mL) and the reaction mixture was heated to 165-170° C. under N2 for 12 h. Reaction was monitored by TLC. After 8.0 h TLC indicated no starting material. The reaction mixture was poured in to ice cold water and solids were filtered. The crude product was purified by column chromatography to give compound 22 as light yellow solid.

Workup

  1. customReaction
  2. additionThe reaction mixture was poured in to ice cold water and solids
  3. filtrationwere filtered
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-43369921f7354f67af9c5781a203ee67
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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