Aluminum(III) Chloride → HCID 136016305, compound

HRID 2112489Notes

Reaction equation

HRID 2112489 reaction equation
[Br:1][C:2]1[C:3]([O:21]C)=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1.[Cl-].[Cl-].[Cl-].[Al+3]>ClCCCl>[Br:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]2[NH:11][C:10](=[O:12])[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[C:6]=2[CH:20]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 57642322HCID 57642322, compound

Product 1

HCID 136016305HCID 136016305, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 1.00 g (0.0263 mole) of 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-methoxy-2H-1,4-benzodiazepin-2-one (Id) in 85 mL of 1,2-dichloroethane was stirred overnight with 1.053 g (0.0079 mole) of aluminum trichloride. An additional 1.00 g of aluminum trichloride was added, and the mixture stirred overnight, after which time the mixture was poured into ice water. The mixture was extracted with dichloromethane-methanol, and the organic layer washed twice with water and then dried over anhydrous sodium sulfate. The solution was concentrated under reduced pressure to provide 0.700 g of 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-8-hydroxy-2H-1,4-benzodiazepin-2-one (Ipp) (MH+/Z=465), which was of sufficient purity to be used in the next step.

Workup

  1. extractionThe mixture was extracted with dichloromethane-methanol
  2. washthe organic layer washed twice with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a486f0bb4eb44e1aaf0a96a7bb5ce189
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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