Salicylamide → HCID 14146191, compound

HRID 1637309Notes

Reaction equation

HRID 1637309 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC1C=CC(C)=CC=1.[C:21]([NH2:30])(=[O:29])[C:22]1[C:23](=[CH:25][CH:26]=[CH:27][CH:28]=1)O>CC(N(C)C)=O>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]2[O:9][C:28]3[CH:27]=[CH:26][CH:25]=[CH:23][C:22]=3[C:21](=[O:29])[N:30]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 5147SalicylamideHCID 7809P-Xylene2×HCID 85024-Nitrobenzoyl chloride

Product 1

HCID 14146191HCID 14146191, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

36.6 g of 4-nitrobenzoyl chloride are added to 48 g of p-xylene over 5 minutes and the suspension warmed to 80° C. To this suspension is then added, over 90 minutes, at 80° C., a solution of 13.2 g of salicylic acid amide in 7.2 g of dimethylacetamide, with stirring. The temperature is then raised to 135° C. over 1 hour and the mixture stirred at this temperature for a further 6 hours. After this time, the mixture is treated with 48 g of p-xylene, cooled to 80° C., the precipitated solids filtered, washed with p-xylene and dried, to yield 25.87 g of 2-(4-nitrophenyl)-4H-1,3-benzoxazin-4-one melting at 249-251° C. and having the following elemental analysis:

Workup

  1. additionTo this suspension is then added, over 90 minutes, at 80° C.
  2. temperatureThe temperature is then raised to 135° C. over 1 hour
  3. temperaturecooled to 80° C.
  4. filtrationthe precipitated solids filtered
  5. washwashed with p-xylene
  6. customdried

Sources & evidence

ORD record
ord-78b78a118e654f8a9626903046f5e3ec
Source dataset
uspto-grants-2000_03
Patent number
US06040443

Reaction notes

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