Phosphorus oxychloride → HCID 54078769, compound

HRID 1196993Notes

Reaction equation

HRID 1196993 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7]([CH3:49])[CH2:8][CH2:9][CH2:10][C:11]1(O)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][O:14][C:13]2[CH:22]=[CH:23][C:24]([CH2:26][CH2:27][O:28][C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][C:12]1=2>N1C=CC=CC=1>[CH3:49][N:7]([CH3:6])[CH2:8][CH2:9][CH:10]=[C:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[CH2:15][O:14][C:13]2[CH:22]=[CH:23][C:24]([CH2:26][CH2:27][O:28][C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:25][C:12]1=2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15749400HCID 15749400, compound

Product 1

HCID 54078769HCID 54078769, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In this process, 1.2 g of 11-(3-dimethylaminopropyl)-11-hydroxy-2-(2-triphenylmethyloxyethyl)-6,11-dihydrodibenz[b,e]oxepin is dissolved in 50 ml of pyridine. To the solution is dropwise added 0.8 g of phosphorusoxychloride under a nitrogen atmosphere and ice-cooling. After stirring the mixture at room temperature for one hour, the solvent is distilled away under reduced pressure. The residue is extracted with 100 ml of methylene chloride, and washed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order. After drying the mixture over anhydrous sodium sulfate, the solvent is distilled away under reduced pressure. The resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethylacetate:triethylamine=10:10:1 ) to obtain 0.82 g of the desired product as a colorless oily matter.

Workup

  1. temperatureice-cooling
  2. distillationthe solvent is distilled away under reduced pressure
  3. extractionThe residue is extracted with 100 ml of methylene chloride
  4. washwashed with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution in order
  5. dry with materialAfter drying the mixture over anhydrous sodium sulfate
  6. distillationthe solvent is distilled away under reduced pressure
  7. customThe resultant residue is purified by column chromatography on silica gel (eluent: hexane:ethylacetate:triethylamine=10:10:1 )

Sources & evidence

ORD record
ord-3ebaaaabe3194e10b0b1e959e45e33b6
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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