Aluminum(III) Chloride → HCID 136016309, compound

HRID 2112491Notes

Reaction equation

HRID 2112491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:21]#[N:22])[C:17]([O:19]C)=[CH:18][C:13]=2[NH:12][C:11](=[O:23])[CH2:10][N:9]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:21]#[N:22])[C:17]([OH:19])=[CH:18][C:13]=2[NH:12][C:11](=[O:23])[CH2:10][N:9]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride3×HCID 57642316HCID 57642316, compound

Product 1

HCID 136016309HCID 136016309, compoundYield 138.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1.2 g (0.0037 mole) of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-methoxy-2H-1,4-benzodiazepin-2-one (Ib, prepared in Example 30) in 100 mL of 1,2-dichloroethane was stirred with 2.5 g (0.0187 mole) of aluminum trichloride at 42° C. for 8 hours, after which an additional 2.5 g of aluminum trichloride was added. Heating and stirring was continued for another 48 hours after which time an additional 2.5 g of aluminum trichloride was added. After 6 hours, the mixture was cooled and then poured onto ice water. The water was extracted with dichloromethane-methanol-tetrahydrofuran (80:10:10), and the extract washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1.6 g of crude 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq). Purification by silica gel chromatography, eluting with ethyl acetate-methanol (90:10) yielded 1.17 g of 5-(2-chlorophenyl)-7-cyano-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Iqq) (MH+/Z=312) which was of sufficient purity for use in the next step.

Workup

  1. temperatureHeating
  2. waitAfter 6 hours
  3. temperaturethe mixture was cooled
  4. additionpoured onto ice water
  5. extractionThe water was extracted with dichloromethane-methanol-tetrahydrofuran (80:10:10)
  6. washthe extract washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-11fb8d684ca94f848686dab6e88707c6
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

Loading…