Salicylamide → HCID 776579, compound

HRID 1637308Notes

Reaction equation

HRID 1637308 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=O)=[CH:15][CH:14]=1>C(O)(C)C>[CH3:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]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:15][CH:14]=1

Participants

4

Reactant 2

HCID 5147SalicylamideHCID 7477p-Anisoyl chloride

Product 1

HCID 776579HCID 776579, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

6.85 g (50 mmol) of salicylic acid amide are added, dropwise, to 18.1 g of p-methoxybenzoyl chloride and the mixture is heated to 150° C. The mixture is then stirred for 30 minutes at this temperature. After cooling, the honey-like mass is stirred with 100 ml of isopropanol, the precipitated solid filtered off and dried to yield 10.2 g of 2-(4-methoxyphenyl)-4H-1,3-benzoxazin-4-one as a white solid melting at 175-178° C. and having the following elemental analysis:

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated solid filtered off
  3. customdried

Sources & evidence

ORD record
ord-bbbbae17ac964de7a7498d5638383439
Source dataset
uspto-grants-2000_03
Patent number
US06040443

Reaction notes

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