Thionyl Chloride → HCID 14127189, compound

HRID 1196988Notes

Reaction equation

HRID 1196988 reaction equation
[CH3:1][C:2]([NH:6][C:7]([C:9]1[CH:24]=[CH:23][C:12]2[O:13][CH2:14][C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[C:17](=[O:18])[C:11]=2[CH:10]=1)=O)([CH3:5])[CH2:3][OH:4].S(Cl)(Cl)=O>C(Cl)Cl>[CH3:1][C:2]1([CH3:5])[CH2:3][O:4][C:7]([C:9]2[CH:24]=[CH:23][C:12]3[O:13][CH2:14][C:15]4[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=4[C:17](=[O:18])[C:11]=3[CH:10]=2)=[N:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14127188HCID 14127188, compound

Product 1

HCID 14127189HCID 14127189, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In this process, 8.0 g of N-(1,1-dimethyl-2-hydroxyethyl)-11-oxo-6,11-dihydrodibenz[b,e]oxepin-2-carboxamide is suspended in 100 ml of methylene chloride. To the suspension is added 3.6 g of thionyl chloride under a nitrogen atmosphere and ice-cooling and the mixture is stirred at room temperature for one hour. To the mixture is added 300 ml of methylene chloride, and the mixture is washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solvent is distilled away under reduced pressure and the residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=2:1 ). The resultant crude product is recrystallized from hexane to obtain 6.3 g of the desired product as a white crystal.

Workup

  1. temperatureice-cooling
  2. washthe mixture is washed with saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent is distilled away under reduced pressure
  5. customthe residue is purified by column chromatography on silica gel (eluent: hexane:ethyl acetate=2:1 )
  6. customThe resultant crude product is recrystallized from hexane

Sources & evidence

ORD record
ord-fc942880150d4da4bce8f5a4496d1e6a
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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