N-Phenyl-p-phenylenediamine → HCID 9814010, compound

HRID 352330Notes

Reaction equation

HRID 352330 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18].Br.C1(NC2C=CC(N)=CC=2)C=CC=CC=1>C(#N)C>[NH:7]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][CH:16]2[CH2:21][CH2:20][O:19][C:17]2=[O:18])=[CH:10][CH:9]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 131724457HCID 131724457, compound

Product 1

HCID 9814010HCID 9814010, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.84 g (10 mmoles) of N1-phenyl-1,4-benzenediamine and 0.41 ml (5 mmoles) of α-bromo-γ-butyrolactone in 20 ml of acetonitrile is heated under reflux for 5 hours. After returning to 20° C., the precipitate which appears during the reaction (N1-phenyl-1,4-benzenediamine hydrobromide) is filtered and rinsed with 20 ml of acetonitrile. The filtrate is concentrated to dryness under vacuum and the residue is purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 4/6). Beige powder. Melting point: 142.5-143° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. customAfter returning to 20° C.
  4. filtrationis filtered
  5. washrinsed with 20 ml of acetonitrile
  6. concentrationThe filtrate is concentrated to dryness under vacuum
  7. customthe residue is purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 4/6)

Sources & evidence

ORD record
ord-97014b1b27d74e67b887cb4af94907c1
Source dataset
uspto-grants-2004_06
Patent number
US06747024B1

Reaction notes

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