N-Phenyl-p-phenylenediamine → 22325-80-0

HRID 1781157Notes

Reaction equation

HRID 1781157 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.C([O-])(O)=O.[Na+].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C(Cl)Cl>[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:20](=[O:23])[CH2:21][CH3:22])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 62324Propionyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 85380522325-80-0Yield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 1.84 g (10.0 mmol, 1 eq.) of commercial N-phenyl-1,4-phenylenediamine (a black solid) and 1.18 g (14.0 mmol, 1.4 eq.) of NaHCO3 in 40 mL of CH2Cl2 was cooled to 0° C. To this suspension was added a solution of 0.96 mL (11.0 mmol, 1.1 eq.) of propionyl chloride in 10 mL of CH2Cl2 dropwise. The ice bath was removed and the mixture stirred for 1 hour and then poured into a seperatory funnel containing 50 mL of each CH2Cl2 and water. The organic phase was separated and extracted with 50 mL of saturated aqueous NaHCO3 solution, dried over MgSO4, filtered and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 1:1 ethyl acetate-hexanes to give 1.79 g (75%) of the product. 1H NMR (300MHz, CDCl3) δ 7.41 (d, 2H), 7.21-7.43 (m, 2H), 7.14 (bs, 1H), 6.96-7.07 (m, 4H), 6.90 (t, 1H), 5.66 (bs, 1H), 2.38 (q, 2H), 1.25 (t, 3H). MS (DCl) m/e 258 (M+NH4 +), 241 (M+H+).

Workup

  1. customThe ice bath was removed
  2. additionpoured into a seperatory funnel
  3. additioncontaining 50 mL of each CH2Cl2 and water
  4. customThe organic phase was separated
  5. extractionextracted with 50 mL of saturated aqueous NaHCO3 solution
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography on silica gel eluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record
ord-d70c7cbd86ba4263a4a1b2bc04c28803
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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