Benzene → HCID 19008590, compound

HRID 1742190Notes

Reaction equation

HRID 1742190 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13]([OH:15])=[O:14])[O:12][C:7]=2[CH:6]=1.S(Cl)(Cl)=O.[CH:33]1C=CC=CC=1>>[Cl:1][C:2]1[CH:24]=[C:23]([C:25]([F:26])([F:27])[F:28])[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:20]=[CH:19][C:8]2[N:9]([CH3:18])[C:10](=[O:17])[C:11]([CH3:16])([C:13]([O:15][CH3:33])=[O:14])[O:12][C:7]=2[CH:6]=1

Participants

4

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 19008591HCID 19008591, compound2×

Product 1

HCID 19008590HCID 19008590, compound

Procedure

7-(2-Chloro-4-trifluoromethylphenoxy)-2,4-dimethyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-2-carboxylic acid (Compound 23) (0.4 g) was dissolved in benzene (10 ml), and thionyl chloride (2 ml) was added thereto, followed by heating under reflux for 3 hours. The solvent was then evaporated under a reduced pressure, methanol (5 ml) was added thereto, and the mixture was stirred at room temperature for one hour. The solvent was then evaporated under a reduced pressure, and the residue was purified by use of silica gel chromatography (eluant: n-hexane/ethyl acetate= 3/1) to give 0.2 g of the title compound (colorless crystals).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customThe solvent was then evaporated under a reduced pressure, methanol (5 ml)
  4. additionwas added
  5. customThe solvent was then evaporated under a reduced pressure
  6. customthe residue was purified by use of silica gel chromatography (eluant: n-hexane/ethyl acetate= 3/1)

Sources & evidence

ORD record
ord-8c532a59c9ce42f38cf13ce56b93ce27
Source dataset
uspto-grants-1994_08
Patent number
US05338719

Reaction notes

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