2-Benzylphenyl isocyanate → 5,11-dihydro-6H-dibenzo[b,e]azepin-6-one

HRID 599507Notes

Reaction equation

HRID 599507 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]=[C:19]=[O:20])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CC1C=CC=CC=1C>[CH:17]1[C:12]2[CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:19](=[O:20])[NH:18][C:13]=2[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 49908342-Benzylphenyl isocyanateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2865185,11-dihydro-6H-dibenzo[b,e]azepin-6-oneYield 34%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of anhydrous aluminum chloride (319 mg, 2.39 mmol) in o-xylene is heated to 110° C. Then, a solution of 2-benzylphenylisocyanate (500 mg, 2.39 mmol) is added dropwise and the brown reaction mixture is kept stirring at 150° C. during 1 h. After cooling to rt, the solvent is evaporated, the residue is dissolved in dichloromethane/methanol (19:1) and filtered through a small plug of silica gel. The solvent is evaporated and the crude product is recrystallized from acetonitrile to give pure subtitle compound as a beige solid (170 mg) in 34% yield (Warawa et al., J. Med. Chem. 2001, 44, 372-389): tR (LC-2) 1.87 min; ESI-MS(+): m/z 210.13 [M+H]+ (calcd 209.24 for C14H11NO).

Workup

  1. temperatureAfter cooling to rt
  2. customthe solvent is evaporated
  3. dissolutionthe residue is dissolved in dichloromethane/methanol (19:1)
  4. filtrationfiltered through a small plug of silica gel
  5. customThe solvent is evaporated
  6. customthe crude product is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-87c6a7808c424f4d8938497c786373fb
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Reaction notes

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