Dimethylformamide → HCID 13341945, compound

HRID 2286853Notes

Reaction equation

HRID 2286853 reaction equation
CN(C)[CH:3]=[O:4].S(Cl)(Cl)=O.[Cl:10][C:11]([Cl:24])([Cl:23])[CH:12]1[NH:17][C:16](=[O:18])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13]1>O>[CH:3]([N:17]1[C:16](=[O:18])[C:15]2[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=2[O:13][CH:12]1[C:11]([Cl:10])([Cl:23])[Cl:24])=[O:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 590558HCID 590558, compound

Product 1

HCID 13341945HCID 13341945, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylformamide (20 ml.) and thionyl chloride (5 ml.) were stirred together, 3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one (2.0 g.) was added in small portions over 15 minutes, and the mixture was stirred at ambient temperature for 48 hours. The reaction mixture was added to water (100 ml.), stirred for 1 hour and filtered. The solid product was dissolved in toluene, and purified by column chromatography on "Kieselgel"-60 (trade mark), eluting with a mixture of 5% by volume of ethyl acetate in toluene. The solvent was evaporated, and the product was crystallised from petroleum ether (b.p. 60°-80° C.) to give 3-formyl-3,4-dihydro-2-trichloromethyl-2H-benzo[e]-[1,3]-oxazin-4-one, m.p. 114° C.

Workup

  1. stirringstirred for 1 hour
  2. filtrationfiltered
  3. dissolutionThe solid product was dissolved in toluene
  4. custompurified by column chromatography on "Kieselgel"-60 (trade mark)
  5. washeluting with a mixture of 5% by volume of ethyl acetate in toluene
  6. customThe solvent was evaporated
  7. customthe product was crystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-c0a53fb5e4c4461797572b9086e521fd
Source dataset
uspto-grants-1981_05
Patent number
US04268510

Reaction notes

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