Acetic Anhydride → 2-[(4-Cyanophenyl)methylene]-2H-1,4-benzoxazin-3(4H)-one

HRID 1825737Notes

Reaction equation

HRID 1825737 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[O:11]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:13](=[O:21])[CH2:12]1.C(OC(=O)C)(=O)C>C(N(CC)CC)C>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:12]2[C:13](=[O:21])[NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:11]2)=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 660424-CyanobenzaldehydeHCID 727572H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 571807642-[(4-Cyanophenyl)methylene]-2H-1,4-benzoxazin-3(4H)-one

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Cyanobenzaldehyde (1.98 g, 0.015 mol) was added to a mixture of 2H-1,4-benzoxazin-3(4H)-one (1.49 g, 0.01 mol), acetic anhydride (4 ml) and triethylamine (2 ml). The reaction mixture was refluxed for 7 h, left overnight at room temperature and poured into crushed ice. The precipitated solid was collected by filtration and washed with acetonitrile. The crude product was purified by recrystalization from DMF:ethanol.

Workup

  1. temperatureThe reaction mixture was refluxed for 7 h
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with acetonitrile
  6. customThe crude product was purified by recrystalization from DMF

Sources & evidence

ORD record
ord-5746300fb5824d5084dc4a65723e13e5
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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