Methyl iodide → HCID 13341946, compound

HRID 2286866Notes

Reaction equation

HRID 2286866 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.[OH-].[Na+].I[CH3:19]>C(O)C>[CH3:19][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]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 590558HCID 590558, compound

Product 1

HCID 13341946HCID 13341946, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3,4-Dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one (prepared as described in Example 3--5 g.) was suspended in ethanol (100 ml.), 63 ml. of a solution of sodium hydroxide (1.0 g.) in ethanol (83 ml.) was added, and the mixture was stirred for 15 minutes to obtain a clear solution. Iodomethane (5 ml.) was added, and the solution was boiled under reflux for 30 minutes. The solvents were evaporated, and the residue was dissolved in a mixture of toluene and ethyl acetate (7:3 by volume) and chromatographed on silica, eluting with the same solvent mixture. The first 100 ml. of eluate was collected, the solvent was evaporated and the residue crystallised on trituration with petroleum ether (b.p. 60°-80° C.) to give 3,4-dihydro-3-methyl-2-trichloromethylbenzo[e]-[1,3]-oxazin-4-one, m.p. 82°-84° C.

Workup

  1. customto obtain a clear solution
  2. temperatureunder reflux for 30 minutes
  3. customThe solvents were evaporated
  4. dissolutionthe residue was dissolved in a mixture of toluene and ethyl acetate (7:3 by volume)
  5. customchromatographed on silica
  6. washeluting with the same solvent mixture
  7. customof eluate was collected
  8. customthe solvent was evaporated
  9. customthe residue crystallised on trituration with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-03e189e7be6f4b1b90e2c46c3619fd75
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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