Phosphorus trichloride → HCID 13280954, compound

HRID 1903624Notes

Reaction equation

HRID 1903624 reaction equation
P(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:28]=[CH:27][C:9]2[C:10]3[C:25](=[O:26])[NH:24][CH2:23][C:11]=3[CH2:12][N+:13]([O-])=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:8]=2[CH:7]=1>C(Cl)Cl>[Cl:5][C:6]1[CH:28]=[CH:27][C:9]2[C:10]3[C:25](=[O:26])[NH:24][CH2:23][C:11]=3[CH2:12][N:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:21])[C:8]=2[CH:7]=1

Participants

4

Reactant 2

HCID 24387Phosphorus trichlorideHCID 13280962HCID 13280962, compound

Product 1

HCID 13280954HCID 13280954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In one portion, 2 ml (2.3 mmol) of phosphorous trichloride were added to a solution of 1.0 g (2.7 mmol) of 8-chloro-6-(2-chlorophenyl)-3,4-dihydropyrrolo[3,4-d][2]benzazepine-1(2H)-one-5-oxide in 200 ml of methylene chloride and refluxed for 1 hour. The mixture was concentrated at reduced pressure. The residue was dissolved in methylene chloride and neutralized with saturated aqueous sodium bicarbonate solution. The methylene chloride solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to give a dark red residue. Purification of the residue by column chromatography (silica gel, 20 g; eluent, 5% methanol in methylene chloride) followed by crystallization from ethyl acetate gave 8-chloro-6-(2-chlorophenyl)-3,4-dihydropyrrolo[3,4-d][2]benzazepin-1(2H)-one as pale yellow prisms solvated with 0.5 mole ethyl acetate, mp 195°-197° C.

Workup

  1. temperaturerefluxed for 1 hour
  2. concentrationThe mixture was concentrated at reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride and neutralized with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe methylene chloride solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customto give a dark red residue
  7. customPurification of the residue by column chromatography (silica gel, 20 g; eluent, 5% methanol in methylene chloride)
  8. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-21aac347648146539dadd98228d33c79
Source dataset
uspto-grants-1984_03
Patent number
US04436662

Reaction notes

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