N,N-Dimethylethylenediamine → HCID 59529894, compound

HRID 1410240Notes

Reaction equation

HRID 1410240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13](F)=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].C([O-])(O)=O.[Na+]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][C:13]([NH:25][CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 516892Sodium BicarbonateHCID 3651415HCID 3651415, compound

Product 1

HCID 59529894HCID 59529894, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of N-(4-bromophenyl)-4-fluoro-3-nitrobenzamide (400 mg; 1.18 mmol) and 2-dimethylamino ethylamine (208 mg; 2.36 mmol) in EtOH (5 mL) was stirred over night at 50° C. The mixture was then poured into aqueous NaHCO3 and extracted with EtOAc. The organic layers were dried over Na2SO4, filtered and concentrated. Recrystallization from EtOAc/petroleum ether gave the crude sub-title compound (560 mg).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customRecrystallization from EtOAc/petroleum ether

Sources & evidence

ORD record
ord-7da4c4976f3c481d99d461816a44023f
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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