N,N-Diethyl-p-phenylenediamine → HCID 178463832, compound

HRID 268251

Reaction equation

HRID 268251 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.[CH2:23]([N:25](CC)[C:26]1C=CC(N)=C[CH:27]=1)[CH3:24]>C(O)C>[ClH:1].[CH2:23]([N:25]([CH2:26][CH3:27])[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)[CH3:24]

Participants

4

Reactant 2

HCID 7120N,N-Diethyl-p-phenylenediamineHCID 178428198HCID 178428198, compound

Product 1

HCID 178463832HCID 178463832, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 26.4 g. (0.122 m.) of the compound of Example I, C. 20 g. (0.122 m.) of N,N-diethyl-p-phenylenediamine and 200 ml. of ethanol was stirred and heated at reflux overnight. The solution was concentrated in vacuo to give 43 g. m.p. 293°-295°. The crude product was recrystallized from 500 ml. of MeOH and precipitated with the addition of 500 ml. of ether. The yield after oven-drying (100°) was 33 g. m.p. 297°-299°.

Workup

  1. additionA mixture of 26.4 g
  2. temperatureheated
  3. temperatureat reflux overnight
  4. concentrationThe solution was concentrated in vacuo
  5. customto give 43 g
  6. customThe crude product was recrystallized from 500 ml
  7. customof MeOH and precipitated with the addition of 500 ml
  8. customThe yield
  9. customafter oven-drying (100°)

Sources & evidence

ORD record
ord-919d3a5b676549188d07391b34b5e3c2
Source dataset
uspto-grants-1976_03
Patent number
US03947434

Linked notes

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