Bromobenzene → 8-Chloro-1-phenyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

HRID 2373363Notes

Reaction equation

HRID 2373363 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][C:8](=[O:13])[NH:7][C:6]=2[CH:14]=1.C([O-])([O-])=O.[K+].[K+].[C:21]1(Br)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CNCCNC>[Cu]I.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][CH2:9][C:8](=[O:13])[N:7]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:6]=2[CH:14]=1

Participants

7

Reactant 4

HCID 7961BromobenzeneHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 11390173HCID 11390173, compound

Product 1

HCID 669346808-Chloro-1-phenyl-3,4-dihydro-1H-benzo[b]azepine-2,5-dione

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

8-Chloro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (iv-j) (500 mg, 2.4 mmol) was combined with K2CO3 (660 mg, 4.8 mmol) under an atmosphere of argon. Phenylbromide (370 mg, 2.4 mmol) and N,N′-Dimethyl-ethane-1,2-diamine (21 mg, 0.24 mmol, 10 mol %) were added, followed by 10 mL of toluene. The mixture was degassed with an argon sparge for 10 min. CuI (23 mg, 0.12 mmol, 5 mol %) was added and the reaction was heated to 110° C. for 48 h. The mixture was filtered and volatiles removed in vacuo. Chromatographic purification provided the desired product containinated with 10% 8-chloro-3,4-dihydro-1H-benzo[b]azepine-2,5-dione (172 mg, 34%) MS m/z═286 (M+1).

Workup

  1. customThe mixture was degassed with an argon
  2. customsparge for 10 min
  3. filtrationThe mixture was filtered
  4. customvolatiles removed in vacuo
  5. customChromatographic purification

Sources & evidence

ORD record
ord-a4975374e0654e1abf23b7beed0c1305
Source dataset
uspto-grants-2008_12
Patent number
US07459448B2

Reaction notes

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