4-Ethoxyaniline → HCID 178466723, compound

HRID 268253Notes

Reaction equation

HRID 268253 reaction equation
[ClH:1].[NH:2]([C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]3[N:21]=[CH:20][NH:19][C:17]3=2)[N:12]=[C:11]([CH3:22])[CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:23][CH2:24][O:25]C1C=CC(N)=CC=1>C(O)C>[ClH:1].[CH3:23][CH2:24][O:25][C:6]1[CH:7]=[CH:8][C:3]([NH:2][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]4[N:21]=[CH:20][NH:19][C:17]4=3)[N:12]=[C:11]([CH3:22])[CH:10]=2)=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 90764-EthoxyanilineHCID 178428198HCID 178428198, compound

Product 1

HCID 178466723HCID 178466723, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 33 g. (0.15 mole) of the compound of Example I, C. and 23 g. (0.15 mole) of p-phenetidine in 1800 ml. of ethanol was refluxed for 6 hr. The solvent was removed by evaporation in vacuo and the residue was slurried with ether. The crude solid was collected by filtration and was recrystallized from ethanol. The product was collected as yellow needles melting at 229°-230° in a yield of 19 g. (36%). Recrystallization from ethanol raised the melting point to 330°-331°.

Workup

  1. additionA mixture of 33 g
  2. customThe solvent was removed by evaporation in vacuo
  3. filtrationThe crude solid was collected by filtration
  4. customwas recrystallized from ethanol
  5. customThe product was collected as yellow needles melting at 229°-230° in a yield of 19 g
  6. customRecrystallization from ethanol
  7. temperatureraised the melting point to 330°-331°

Sources & evidence

ORD record
ord-779fea33c9434a52ad16020b323711e0
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Reaction notes

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