Salicylic Acid → 2-Phenyl-4H-1,3-benzoxazin-4-one

HRID 1637307Notes

Reaction equation

HRID 1637307 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:11](Cl)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C1C(=CC=CC=1)O>C(OCC)C>[C:12]1([C:11]2[O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:9])[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 5147SalicylamideHCID 7412Benzoyl chloride

Product 1

HCID 5554072-Phenyl-4H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.85 g (50 mmol) of salicylic acid amide are added, dropwise, to 11.5 ml of benzoyl chloride and the mixture is heated to 170° C. The mixture is then stirred for 30 minutes at this temperature. During this time, the salicylic acid dissolves to produce, on cooling, a honey-like mass which is then stirred with diethyl ether to yield a white solid which is filtered off, washed with diethyl ether and dried. There are obtained 8.78g of 2-phenyl-4H-1,3-benzoxazin-4-one as a white powder melting at 104-105° C. and having the following elemental analysis:

Workup

  1. customto produce
  2. temperatureon cooling
  3. customto yield a white solid which
  4. filtrationis filtered off
  5. washwashed with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-8bedd4f817d448b7a3acb73583b43a6b
Source dataset
uspto-grants-2000_03
Patent number
US06040443

Reaction notes

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