Potassium Carbonate → HCID 10668079, compound

HRID 343172Notes

Reaction equation

HRID 343172 reaction equation
[CH:1]([N:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[C:5](=[O:8])[CH2:6]Br)([CH3:3])[CH3:2].[C:17]1([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[NH2:30])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]([N:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])[C:5](=[O:8])[CH2:6][NH:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 10755599HCID 10755599, compound

Product 1

HCID 10668079HCID 10668079, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-Isopropyl-N-(2-methoxy-phenyl) bromoacetamide, prepared as in Part B, (10.0 g 34.9 mmol), N-phenyl phenylenediamine (6.41 g, 34.9 mmol) and potassium carbonate (4.82 g) in DMF (100 mL) is stirred at RT for 48 h. The reaction mixture is filtered through celite and the filtrate concentrated in vacuo. Purification by silica gel flash column chromatography using 20% ethyl acetate in hexane as eluent gave N-Isopropyl-N-(2-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamideas a light brown foam (4.50 g): 1H NMR (300 MHz, CDCl3) δ7.46 (t, 1H, J=7.9), 7.030-7.05 (m, 8H), 6.98 (t, 1H, J=6.8), 6.84 (m, 2H), 6.70 (t, 1H, J=7.6), 6.37 (d, 1H, J=8.0), 5.4 (s, br, 1H), 4.95 (m, 1H, J=6.8), 3.84 (s, 3H), 3.45 (dd, 2H, J=23.2, 6.6), 1.20 (d, 3H, J=6.8), 1.01 (d, 3H, J=6.8).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-daa16c3ed8544cf4bffc12a0147ea8e4
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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