Potassium Carbonate → HCID 21201820, compound

HRID 1979310Notes

Reaction equation

HRID 1979310 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][CH2:4][CH:3]1[NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cu].[Cu](I)I>[C:25]1([N:8]2[C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[NH:5][CH2:4][CH:3]([NH:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])[C:2]2=[O:1])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 21201576HCID 21201576, compound

Product 1

HCID 21201820HCID 21201820, compoundYield 58.2%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 83717Copper iodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

2-Oxo-3-benzyloxycarbonylamino-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (1.38 g) was dissolved in N,N-dimethylformamide (20 ml), iodobenzene (1.36 g), copper powder (286 mg), copper iodide (446 mg) and potassium carbonate (622 mg) were added, the mixture was stirred at 150° C. for 2 hours. The insoluble material was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), to thereby obtain 1.00 g of the title compound.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-1888de1b828f46208368e6183d3c488b
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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