Water → HCID 10622394, compound

HRID 343126Notes

Reaction equation

HRID 343126 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].BrC[CH2:23][C:24]([N:26]([CH:37]([CH3:39])[CH3:38])[C:27]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=1)=[O:25].O>CN(C=O)C>[CH:37]([N:26]([C:27]1[CH:28]=[CH:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=1)[C:24](=[O:25])[CH2:23][NH:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([CH3:39])[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68297N-Phenyl-o-phenylenediamineHCID 54198719HCID 54198719, compound

Product 1

HCID 10622394HCID 10622394, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1.16 g (6.32 mmol) of N-Phenyl phenylenediamine in 15 mL of DMF is added 1.05 g (7.58 mmol, 1.2 equiv) of K2CO3 and 2.05 g (6.32 mmol) of Bromomethyl-N-isopropyl-N-(4-trifluoromethyl-phenyl) acetamide. The resulting mixture is stirred 1 h at RT then is heated to 50° C. for 16 h. The reaction mixture is then cooled to RT, poured into 100 mL H2O and extracted with Et2O (2×100 mL). The organic layers were washed in series with 1N HCl (2×80 mL), NaHCO3 (1×80 mL), and H2O (1×80 mL), dried (MgSO4), and the solvent removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 5/1 as eluent afforded 2.05 g of N-Isopropyl-2-(2-phenylamino-phenylamino)-N-(4-trifluoromethyl-phenyl)-acetamide as a light tan solid: 1H NMR (CDCl3, 400 MHz) δ7.72 (d, 2H, J=8.2), 7.26 (d, 2H, J=8.2), 7.15 (m, 3H), 6.95 (dd, 1H, J=7.7, 7.7), 6.80 (dd, 1H, J=7.1, 7.1), 6.74 (d, 2H, J=7.9), 6.68 (dd, 1H, J=7.4, 7.4), 6.29 (d, 1H, J=7.9), 5.20 (s, 1H), 5.00 (m, 1H), 3.40 (s, 2H), 1.06 (d, 6H, J=6.6); low resolution MS (FAB)m/e 427 (MH+); high resolution MS (C24H24F3N3O) Calc. 427.1871 Found 427.1871.

Workup

  1. temperaturethen is heated to 50° C. for 16 h
  2. temperatureThe reaction mixture is then cooled to RT
  3. extractionextracted with Et2O (2×100 mL)
  4. washThe organic layers were washed in series with 1N HCl (2×80 mL), NaHCO3 (1×80 mL), and H2O (1×80 mL)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customPurification of the crude material by silica gel flash column chromatography

Sources & evidence

ORD record
ord-d94dd8ab70874db194ed905998a00593
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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