Hydrochloric Acid → HCID 13243503, compound

HRID 482751Notes

Reaction equation

HRID 482751 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:12])[NH:11][C:5]=2[CH:4]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:16].[ClH:21]>C1(C)C(C)=CC=CC=1>[Cl:21][C:9]1([Cl:16])[CH2:8][CH2:7][C:6]2[CH:13]=[CH:14][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[NH:11][C:10]1=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 6769538-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

Product 1

HCID 13243503HCID 13243503, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 8-methoxy-2,3,4,5-tetrahydro-1H[1]benzazepin-2-one (7.0 g, described in Example 14) and phosphorus pentachloride (30.0 g) in xylene (200 ml) was heated with stirring under an atmosphere of nitrogen to 90° (oil bath temperature) during 30 minutes with pauses at 30° and at 50°. There was a copious evolution of hydrogen chloride gas. The temperature was maintained at 90° for 30 minutes. The reaction mixture was filtered while hot to remove a small amount of suspended solid, and the filtrate was evaporated under reduced pressure until all the solvent was removed. The residue was added with stirring to saturated aqueous sodium carbonate (20 ml). The product was filtered after the solidification process was complete, slurried in ethanol (30 ml), washed with ethanol (10 ml) and ether (10 ml) and dried to give 3,3-dichloro-8-methoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one, m.p. 148°-150°.

Workup

  1. customat 50°
  2. temperatureThe temperature was maintained at 90° for 30 minutes
  3. filtrationThe reaction mixture was filtered while hot
  4. customto remove a small amount of suspended solid
  5. customthe filtrate was evaporated under reduced pressure until all the solvent
  6. customwas removed
  7. additionThe residue was added
  8. stirringwith stirring to saturated aqueous sodium carbonate (20 ml)
  9. filtrationThe product was filtered after the solidification process
  10. washwashed with ethanol (10 ml) and ether (10 ml)
  11. customdried

Sources & evidence

ORD record
ord-66b9ac9241d74801a43a3563b9646ba3
Source dataset
uspto-grants-1986_03
Patent number
US04575503

Reaction notes

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