Salicylic Acid → 2-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

HRID 1475614Notes

Reaction equation

HRID 1475614 reaction equation
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].S(Cl)(Cl)=O.[C:15]([NH2:24])(=O)[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)[OH:18]>C1(C)C(C)=CC=CC=1>[OH:18][C:17]1[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=1[C:15]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1](=[O:10])[N:24]=1

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 5147SalicylamideHCID 24386Thionyl Chloride2×

Product 1

HCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
37.5 °C

Procedure

Xylene (1.5 L) and salicylic acid (1 Kg.) was added to a 5 L 4-neck round bottom flask equipped with a mechanical stirrer and thermocouple. Thionyl chloride (1.29 kg) was added at 10° C. to 15° C. After addition of thionyl chloride reaction mass is stirred at 10° C. to 15° C. for 30 minutes. Reaction mass is heated at 35-40° C. for 1 hr. Salicylamide solution (0.891 kg in 2.0 lit of Xylene) was added in reaction mass at 25° C.-30° C. After addition reaction mass was gradually heated at 80° C.-126° C. and stirred for 2 hrs. After the completion of reaction excess of Xylene was distilled out. Methanol was added in the reaction mass at 70° C.-80° C. and stirred for 1 hr. gradually cooled the reaction mass at 25-30° C. Filtered the solid and washed with Methanol and sucked it dry. Dry the obtained solid at 55-60° C. under vacuum tray drier.

Workup

  1. customequipped with a mechanical stirrer
  2. customReaction mass
  3. additionAfter addition reaction mass
  4. temperaturewas gradually heated at 80° C.-126° C.
  5. stirringstirred for 2 hrs
  6. distillationwas distilled out
  7. additionMethanol was added in the reaction mass at 70° C.-80° C.
  8. stirringstirred for 1 hr
  9. temperaturegradually cooled the reaction mass at 25-30° C
  10. filtrationFiltered the solid
  11. washwashed with Methanol
  12. customdry
  13. customDry the obtained solid at 55-60° C. under vacuum tray drier

Sources & evidence

ORD record
ord-b39a84a6c688470690eb53ca775c6e2c
Source dataset
uspto-grants-2015_04
Patent number
US09018389B2

Reaction notes

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