N,N'-Dimethylethylenediamine → HCID 89690578, compound

HRID 2202969Notes

Reaction equation

HRID 2202969 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][NH:12][C:11](=[O:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:17]1[CH:18]=[CH:19][C:20]([N+:25]([O-:27])=[O:26])=[C:21]([CH:24]=1)[NH:22][CH3:23].CNCCNC.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu](I)I>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:17]2[CH:18]=[CH:19][C:20]([N+:25]([O-:27])=[O:26])=[C:21]([NH:22][CH3:23])[CH:24]=2)[C:11](=[O:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 36077244-Benzyloxy-2(1H)-pyridoneHCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 89690578HCID 89690578, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

The mixture of 4-(benzyloxy)pyridin-2(1H)-one (5.0 g), 5-bromo-N-methyl-2-nitroaniline (5.74 g), copper iodide (4.73 g), N,N′-dimethylethylenediamine (2.8 ml) and potassium carbonate (10.30 g) in DMSO (250 ml) was stirred at 150° C. under N2 for 1 h. After cooling to room temperature, 28% NH3solution was added to the resulting mixture. The resulting suspension was filtered. The precipitate was washed with water and IPA and dried to give the title compound (5.1 g) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. addition28% NH3solution was added to the resulting mixture
  3. filtrationThe resulting suspension was filtered
  4. washThe precipitate was washed with water and IPA
  5. customdried

Sources & evidence

ORD record
ord-a6de4db3ae9d4ecba18647ff97cd2bc3
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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