Acetyl chloride → 6-Isopropyl-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 351835Notes

Reaction equation

HRID 351835 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:13])[CH3:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:15](OCC)=[O:16].C(Cl)(=O)C>O1CCOCC1>[CH:11]([C:8]1[CH:9]=[CH:10][C:2]2[NH:1][C:15](=[O:16])[O:5][C:4](=[O:6])[C:3]=2[CH:7]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10928Ethyl chloroformateHCID 125621272-Amino-5-(propan-2-yl)benzoic acid

Product 1

HCID 227135176-Isopropyl-1H-benzo[d][1,3]oxazine-2,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-5-isopropylbenzoic acid (30. g, 16.7 mmol) and ethyl chloroformate (1.75 mL, 18.4 mmol) in dioxane (20 mL) was heated under reflux for 2 h. After cooling, acetyl chloride (1.4 mL) was added and heating under reflux continued for another 3 h. After cooling, the mixture was evaporated and the resulting solid digested with tert-butyl methyl ether: heptane (1:1, 20 mL) by heating under reflux for 1 h. The soild was then filtered off and washed with tert-butyl methyl ether: heptane (1:1, 10 mL). Yield 3.1 g (89%). m/z 204 (M—H−).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. temperatureheating
  5. temperatureunder reflux
  6. temperatureAfter cooling
  7. customthe mixture was evaporated
  8. temperatureby heating
  9. temperatureunder reflux for 1 h
  10. filtrationThe soild was then filtered off
  11. washwashed with tert-butyl methyl ether: heptane (1:1, 10 mL)

Sources & evidence

ORD record
ord-a97350d08dbc4f209455772ec324a17f
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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