Dimethylformamide → HCID 18994512, compound

HRID 375227Notes

Reaction equation

HRID 375227 reaction equation
CN(C)C=O.[C:6]1([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:19]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([N+]([O-])=O)[CH:23]=1)([O-:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[N+:19]([C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[O:18][C:15]1[CH:14]=[CH:13][C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:17][CH:16]=1)([O-:21])=[O:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 71034-HydroxybiphenylHCID 74521,3-DinitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 18994512HCID 18994512, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a four necked flask equipped with a thermometer, reflux condenser and stirrer, 400 g of N,N-dimethylformamide (DMF), 40 g of toluene, 80 g (0.47 mol) of p-phenylphenol, 86.9 g (0.517 mol) of m-dinitrobenzene, and 35.9 g (0.26 mol) of potassium carbonate were charged. The mixture was heated to 140° C. with stirring and aged at 140° C. for 15 hours. After finishing the reaction, the reaction mixture was cooled to 100° C. and filtered to remove inorganic salts. The filtrate was incorporated with 300 g of water and cooled to room temperature to crystallize the desired product. The precipitated crystals were filtered and recrystallized from a mixture of 380 g of DMF and 100 g of water to obtain 96 g (70% yield) of 4-(3-nitrophenoxy)-1,1'-biphenyl (NPBP).

Workup

  1. customTo a four necked flask equipped with a thermometer
  2. temperaturereflux condenser and stirrer
  3. customthe reaction
  4. temperaturethe reaction mixture was cooled to 100° C.
  5. filtrationfiltered
  6. customto remove inorganic salts
  7. temperaturecooled to room temperature
  8. customto crystallize the desired product
  9. filtrationThe precipitated crystals were filtered
  10. customrecrystallized from a mixture of 380 g of DMF and 100 g of water

Sources & evidence

ORD record
ord-b526916842ad4e959dd7096ed7fec22c
Source dataset
uspto-grants-1996_01
Patent number
US05484880

Reaction notes

Loading…