Sodium Carbonate → HCID 13067124, compound

HRID 223492Notes

Reaction equation

HRID 223492 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:28]=[CH:27][C:10]2[C:11]3[C:12](=[CH:23][NH:24][C:25]=3[CH3:26])[CH2:13][N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:9]=2[CH:8]=1.[C:29](=O)([O-])[O-:30].[Na+].[Na+]>CN(C)C=O>[Cl:6][C:7]1[CH:28]=[CH:27][C:10]2[C:11]3[C:12](=[C:23]([CH:29]=[O:30])[NH:24][C:25]=3[CH3:26])[CH2:13][N:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:9]=2[CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 13067111HCID 13067111, compound

Product 1

HCID 13067124HCID 13067124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By means of a syringe 0.6 ml (6.5 mmol) of phosphorous oxychloride was added to a solution of 0.7 g (2.0 mmol) of 8-chloro-6-(2-chlorophenyl)-1-methyl-2H,4H-pyrrolo[3,4-d][2]benzazepine in 8 ml of dimethylformamide which was cooled to 0°. The mixture was stirred at 0° for 1 hr, poured into 50 ml of saturated aqueous sodium carbonate and extracted with methylene chloride. The methylene chloride solution was washed with water, dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a red amorphous solid. Purification by column chromatography (silica gel, 20 g; 4% ether in methylene chloride, eluent) gave an off-white solid. Recrystallization from a mixture of methylene chloride and ethyl acetate gave off-white crystals, mp 274°-276°.

Workup

  1. temperaturewas cooled to 0°
  2. extractionextracted with methylene chloride
  3. washThe methylene chloride solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a red amorphous solid
  7. customPurification by column chromatography (silica gel, 20 g; 4% ether in methylene chloride, eluent)
  8. customgave an off-white solid
  9. customRecrystallization
  10. additionfrom a mixture of methylene chloride and ethyl acetate
  11. customgave off-white crystals, mp 274°-276°

Sources & evidence

ORD record
ord-224bb6ef67c947b4a954b86490159b91
Source dataset
uspto-grants-1982_10
Patent number
US04354973

Reaction notes

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