Hydrochloric Acid → HCID 18997264, compound

HRID 230846Notes

Reaction equation

HRID 230846 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[C:8]([O:13]C)[C:7]=1[C:15](=[O:18])[CH2:16]Cl.Cl.CO>ClCCl>[NH2:5][C:6]1[C:7]2[C:15](=[O:18])[CH2:16][O:13][C:8]=2[CH:9]=[CH:10][C:11]=1[Cl:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6451240Aluminum(III) ChlorideHCID 18997257HCID 18997257, compound

Product 1

HCID 18997264HCID 18997264, compoundYield 132.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred suspension of aluminum chloride (77.6 g) in dry dichloromethane (300 ml) was added dropwise a solution of Intermediate 20 (45 g) in dichloromethane (250 ml). The mixture was heated under reflux for 6 h and then cooled to room temperature. The mixture was decomposed by the dropwise addition of 2M hydrochloric acid, then methanol and dichloromethane were added and the organic layer collected. The aqueous layer was extracted with dichloromethane and the combined organic layers dried over sodium sulphate and concentrated in vacuo. The residue was dissolved in boiling methanol and an excess of triethylamine added. The solvent was removed in vacuo and the residue absorbed onto silica gel. Purification by chromatography on silica gel eluting with a gradient of 20% to 50% ethyl acetate in cyclohexane gave the title compound as an orange/brown solid (46.9 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 h
  3. customthe organic layer collected
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialthe combined organic layers dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved
  8. additionan excess of triethylamine added
  9. customThe solvent was removed in vacuo
  10. customthe residue absorbed onto silica gel
  11. customPurification by chromatography on silica gel eluting with a gradient of 20% to 50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-e1e2b264074b41e0adbc2be0ef1d537e
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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