Acetic Anhydride → HCID 22386582, compound

HRID 2121828Notes

Reaction equation

HRID 2121828 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:5]=[CH:4][N:3]=1.N1C=CC=CC=1.ClCCl.[C:30](OC(=O)C)(=[O:32])[CH3:31]>>[C:30]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:5]=[CH:4][N:3]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 21875418Pyridine methylene chlorideHCID 22386590HCID 22386590, compound

Product 1

HCID 22386582HCID 22386582, compoundYield 45.4%

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 4-amino-5-(4-methoxyphenoxy)quinazoline (1.0 g, 3.7 mmol) in 30 ml of dichloromethane pyridine (0.3 g, 3.7 mmol) and acetic anhydride (0.38 g, 3.7 mmol) were added at room temperature and stirring continued for 4 days. After evaporation under reduced pressure, 30 ml of 2-propanol was added and after cooling to 4° C. the solid was collected by filtration, washed, recrystallized from ethanol, filtrated again and dried at 50° C. in vacuo. to give 4-acetamido-5-(4-methoxyphenoxy)quinazoline (0.5 g, 45.4%, m.p. 174-175° C.).

Workup

  1. customAfter evaporation under reduced pressure, 30 ml of 2-propanol
  2. additionwas added
  3. filtrationwas collected by filtration
  4. washwashed
  5. customrecrystallized from ethanol
  6. filtrationfiltrated again
  7. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-e0d1a6aa3e30428395ec23dd062328d7
Source dataset
uspto-grants-2004_02
Patent number
US06696482B2

Reaction notes

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