4-Aminophenol → 4-({2-[2-(5-Nitrofuran-2-yl)ethenyl]quinazolin-4-yl}amino)phenol

HRID 918241Notes

Reaction equation

HRID 918241 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.CN(C)C=O.[N+:14]([C:17]1[O:21][C:20]([CH:22]=[CH:23][C:24]2[N:33]=[C:32](Cl)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]>O>[N+:14]([C:17]1[O:21][C:20]([CH:22]=[CH:23][C:24]2[N:33]=[C:32]([NH:7][C:6]3[CH:5]=[CH:4][C:3]([OH:8])=[CH:2][CH:1]=3)[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]=2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 4034-Aminophenol2×HCID 6228DimethylformamideHCID 536340792-[2-(5-Nitro-2-furyl)vinyl]-4-chloroquinazoline

Product 1

HCID 540739994-({2-[2-(5-Nitrofuran-2-yl)ethenyl]quinazolin-4-yl}amino)phenolYield 64.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 250 ml Erlenmeyer flask equipped with a magnetic stirrer and oil bath for heating was charged with 8.0 g (0.07 mole) of p-aminophenol and 25 ml of dimethylformamide. After the p-aminophenol was dissolved by stirring, 9.05 g (0.03 mole) of 2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) was added. The reaction mixture was then heated at 70°-90°C for 2 hours after which 60 ml of water was added and the solution after cooling was placed in a refrigerator for crystallization. After three days, the brown yellow solid was collected, washed first with water, then methanol and then dried to obtain 7.20 g of product melting at 250°-60°C with decomposition. Recrystallization from a 1:1 dimethylformamidemethanol mixture gave 6.5 g of orange crystals of the purified product which melted at 270°-2°C with decomposition.

Workup

  1. customA 250 ml Erlenmeyer flask equipped with a magnetic stirrer and oil bath
  2. temperaturefor heating
  3. additionwas added
  4. temperaturethe solution after cooling
  5. customwas placed in a refrigerator for crystallization
  6. customthe brown yellow solid was collected
  7. washwashed first with water
  8. dry with materialmethanol and then dried

Sources & evidence

ORD record
ord-7c6cb48a13ba4fce9b1161de985eb37f
Source dataset
uspto-grants-1976_07
Patent number
US03970648

Reaction notes

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