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

HRID 343114Notes

Reaction equation

HRID 343114 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

Conditions

Temperature
0 °C

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) is stirred at 0° C. for 2 h and then allowed to stir at RT for 20 h. The reaction mixture is filtered through celite and the filtrate concentrated in vacuo The resultant residue is 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 is removed by filtration and washed with cold EtOAc and dried to afford the desired product (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 (29.6 g) of the desired product as a beige solid: 1H NMR (300 MHz, DMSO-d6), δ7.22 (m, 2H), 7.05 (m, 2H), 6.47 (m, 1H), 6.34 (m, 2H), 5.95 (m, 1H), 4.81 (m., 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 is filtered through celite
  3. concentrationthe filtrate concentrated in vacuo The resultant residue
  4. dissolutionis 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. customis removed by filtration
  11. washwashed with cold EtOAc
  12. customdried

Sources & evidence

ORD record
ord-3cd815e1c5cf40fb8dc2ae9d31dd0028
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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