Sodium Carbonate → HCID 13067120, compound

HRID 2296320Notes

Reaction equation

HRID 2296320 reaction equation
P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[CH:27]=[CH:26][C:10]2[C:11]3[C:12](=[CH:23][NH:24][CH:25]=3)[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:28](=O)([O-])[O-:29].[Na+].[Na+]>C(Cl)Cl.CN(C)C=O>[Cl:6][C:7]1[CH:27]=[CH:26][C:10]2[C:11]3[C:12](=[C:23]([CH:28]=[O:29])[NH:24][CH:25]=3)[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

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 135967503HCID 135967503, compound

Product 1

HCID 13067120HCID 13067120, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3.0 ml (33 mmol) of phosphorous oxychloride in 20 ml of methylene chloride was added dropwise to a solution of 3.0 g (9.1 mmol) of 8-chloro-6-(2-chlorophenyl)-2H,4H-pyrrolo[3,4-d][2]benzazepine in 40 ml of dimethylformamide which was cooled to 0°. Stirring at 0° was continued for 2 hr. The mixture was poured into a saturated solution of 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 dryness. Purification by column chromatography (silica gel, 100 g; eluent, 50% (v/v) ethyl acetate in methylene chloride) gave a light pink solid, mp 270°-274°. Recrystallization from a mixture of ethyl acetate and methylene chloride gave peach colored prisms, mp 276°-277°.

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 to dryness
  6. customPurification by column chromatography (silica gel, 100 g; eluent, 50% (v/v) ethyl acetate in methylene chloride)
  7. customgave a light pink solid, mp 270°-274°
  8. customRecrystallization
  9. additionfrom a mixture of ethyl acetate and methylene chloride
  10. customgave peach colored prisms, mp 276°-277°

Sources & evidence

ORD record
ord-d1b3d0306bb8409aba87272c009868e3
Source dataset
uspto-grants-1984_01
Patent number
US04428879

Reaction notes

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