Sodium hydride → HCID 70656511, compound

HRID 69057Notes

Reaction equation

HRID 69057 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Na+].[CH2:21]([N:23]1[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[C:27](=[O:33])[N:26]([CH3:34])[C:25]2[CH:35]=[C:36]([O:39][CH2:40][CH2:41][CH2:42]I)[CH:37]=[CH:38][C:24]1=2)[CH3:22]>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:42][CH2:41][CH2:40][O:39][C:36]2[CH:37]=[CH:38][C:24]3[N:23]([CH2:21][CH3:22])[C:29](=[O:30])[C:28]([CH3:32])([CH3:31])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=3[CH:35]=2)[C:4](=[O:12])[C:3]=1[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27848104-Chloro-3-phenyl-1H-quinoline-2-oneHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 70656511HCID 70656511, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-3-phenyl-1H-quinoline-2-one (0.3 g) was suspended in DMF (6 ml). Sodium hydride (60% in oil) (51 mg) was added, and the mixture was stirred for 15 minutes at room temperature. 1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (0.55 g) was added thereto and the mixture was stirred at room temperature for 7 days. The reaction mixture was poured to ice water (50 ml), and the generated insoluble matter was separated. The insoluble matter was dissolved in ethyl acetate. The liquid was dried over sodium sulfate and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3). The purified product was condensed under reduced pressure, and the residue was recrystallized from ether, thereby obtaining the title compound (0.28 g) as a white powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 7 days
  2. customthe generated insoluble matter was separated
  3. dissolutionThe insoluble matter was dissolved in ethyl acetate
  4. dry with materialThe liquid was dried over sodium sulfate and condensed under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:3)
  6. customcondensed under reduced pressure
  7. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-eddda42932b94501a13323774f1500a5
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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