O-Phenylenediamine → N-Isopropyl-N-(4-methoxy-phenyl)-2-phenylamino acetamide

HRID 1599091Notes

Reaction equation

HRID 1599091 reaction equation
[CH:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:5](=[O:8])[CH2:6]Br)([CH3:3])[CH3:2].[C:17]1(N)[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH2:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:5](=[O:8])[CH2:6][NH:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:17]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 107795342-Bromo-N-isopropyl-N-(4-methoxyphenyl)acetamide

Product 1

HCID 53747552N-Isopropyl-N-(4-methoxy-phenyl)-2-phenylamino acetamideYield 24.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-Isopropyl-N-(4-methoxy-phenyl)bromoacetamide (257.6 g 924 mmol), 1,2-phenylene diamine (100 g, 924 mmol) and potassium carbonate (128 g, 924 mmol) in DMF (1200 ml) was stirred at 0° for 2 h and then allowed to stir at rt for 20 h. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo The resultant residue was dissolved in EtOAc (1200 ml), washed with water (3×200 ml), brine (200 ml), dried (MgSO4) and concentrated in vacuo. After removal of about 70% of the solvent a precipitate formed which was removed by filtration and washed with cold EtOAc and dried to afford the title compound (67.1 g) as a beige solid. The combined filtrates were concentrated in vacuo to afford a dark oil (88 g). Two Recrystallisations from ethanol afforded a second batch of the title compound as a beige solid (29.6 g).1H NMR (300 MHz, DMSO-d6). s 7.22 (m, 2H), 7.05(m, 2H), 6.47 (m, 1H), 6.34 (m, 2H), 5.95 (m, 1H), 4.81 (sept., 1H, J=6.8 ), 4.59 (dt, 1H, J=27.2, 6.1), 4.4 (s, 2H), 3.77 (s, 3H), 3.30 (s, 2H), 0.96 (d, 6H, J =6.8).

Workup

  1. stirringto stir at rt for 20 h
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo The resultant residue
  4. dissolutionwas dissolved in EtOAc (1200 ml)
  5. washwashed with water (3×200 ml), brine (200 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customAfter removal of about 70% of the solvent a precipitate
  9. customformed which
  10. customwas removed by filtration
  11. washwashed with cold EtOAc
  12. customdried

Sources & evidence

ORD record
ord-c06a7c398a8b4d17b580f236a3823b0c
Source dataset
uspto-grants-1998_04
Patent number
US05739129

Reaction notes

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