Potassium Carbonate → HCID 10572426, compound

HRID 343177Notes

Reaction equation

HRID 343177 reaction equation
[CH:1]([N:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)[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]=[C:11]([O:15][CH3:16])[CH:10]=1)[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 10731907HCID 10731907, compound

Product 1

HCID 10572426HCID 10572426, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-Isopropyl-N-(3-methoxy-phenyl) bromoacetamide, prepared as in Part B, (12.0 g 41.9 mmol), N-phenyl phenylenediamine (7.7 g, 41.9 mmol) and potassium carbonate (5.79 g) in DMF (100 mL) is stirred at RT for 20 h. The reaction mixture is filtered through celite and the filtrate diluted with ethyl acetate (150 mL) and washed with water (2×100 mL), 2N hydrochloric acid (2×100 mL), 1N aqueous sodium hydrogen carbonate (100 mL), dried (K2CO3 /MgSO4), and concentrated in vacuo. Purification by silica gel flash column chromatography using 20% ethyl acetate in hexane as eluent gave 8.2 g of N-Isopropyl-N-(3-methoxy-phenyl)-2-(2-phenylamino-phenylamino) acetamide as a light brown foam: 1H NMR (300 MHz, CDCl3) δ7.43 (t, 1H, J=8.0), 7.3-7.1 (m, 3H), 7.02 (m, 2H), 6.9-6.6 (m, 7H), 6.36 (d, 1H, J=7.8), 5.3 (s, br, 1H), 4.95 (m, 1H, J=6.8), 3.88 (s, 3H), 3.53 (s, 2H), 1.06 (m, 6H).

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. additionthe filtrate diluted with ethyl acetate (150 mL)
  3. washwashed with water (2×100 mL), 2N hydrochloric acid (2×100 mL), 1N aqueous sodium hydrogen carbonate (100 mL)
  4. dry with materialdried (K2CO3 /MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-0565b56013e1449f965da6c162c9c665
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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