Acetic Anhydride → HCID 23460474, compound

HRID 2286852Notes

Reaction equation

HRID 2286852 reaction equation
[Cl:1][C:2]([Cl:15])([Cl:14])[CH:3]1[NH:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4]1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>O>[C:16]([N:8]1[C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[O:4][CH:3]1[C:2]([Cl:1])([Cl:14])[Cl:15])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 590558HCID 590558, compound

Product 1

HCID 23460474HCID 23460474, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3,4-Dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one (prepared as described in Example 3--4.0 g.) was stirred with acetic anhydride (40 ml.) on a steam-bath for 10 hours. The reaction mixture was cooled to room temperature, poured into water (400 ml.) and stirred for 3 hours, and the oil which separated was extracted into diethyl ether. The extract was dried and the solvent was evaporated to leave an oil, which was purified by column chromatography on "Kieselgel 60" (trade mark) silica, and the column was eluted with 10% v/v ethyl acetate in toluene. 25 Ml. fractions were collected, fractions 1-7 were combined, and the solvent was evaporated to give 3-acetyl-3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one as an oil. The n.m.r. spectrum in hexadeuterio-dimethylsulphoxide showed the following characteristic peaks (δ values):

Workup

  1. customthe oil which separated
  2. extractionwas extracted into diethyl ether
  3. customThe extract was dried
  4. customthe solvent was evaporated
  5. customto leave an oil, which
  6. customwas purified by column chromatography on "Kieselgel 60" (trade mark) silica
  7. washthe column was eluted with 10% v/v ethyl acetate in toluene
  8. customfractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-55935a657b26415680a3e33f6f223448
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

Loading…