O-Phenylenediamine → 2-(2-Aminophenylamino)-N-isopropyl-N-phenyl acetamide

HRID 343115Notes

Reaction equation

HRID 343115 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]([N:19]([CH:26]([CH3:28])[CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]>C1COCC1.O.CCOC(C)=O>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][CH2:16][C:17]([N:19]([CH:26]([CH3:28])[CH3:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]

Participants

7

Reactant 3

HCID 7243O-PhenylenediamineHCID 11430Potassium CarbonateHCID 152160012-bromo-N-isopropyl-N-phenyl-acetamide

Product 1

HCID 541932642-(2-Aminophenylamino)-N-isopropyl-N-phenyl acetamideYield 65.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 40 g (385 mmol) of phenylenediamine is added 75 g (543 mmol, 1.4 equiv.) of potassium carbonate. The suspension is stirred at RT and a solution of 99 g (386.5 mmol, 1 equiv.) of 2-Bromo-N-isopropyl-N-phenyl acetamide in 15 mL THF is added dropwise. The resulting suspension is stirred at RT for 16 h and diluted with 1 L H2O and 1 L EtOAc. The Organics were washed with H2O (3×500 mL), brine (500 mL), dried (MgSO4), and the solvents removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 8/2 as eluent afforded 71 g of a yellow solid: mp. 110°-112° C.; 1H NMR (CDCl3, 300 MHz) δ7.48-7.44 (m, 4H), 7.18-7.15 (m, 2H), 6.69-6.59 (m, 3H), 6.21-6.19 (m, 1H), 5.11-4.98 (m, 1H), 3.4 (s, 2H), 1.09 (d, 6H, J=7).

Workup

  1. stirringThe resulting suspension is stirred at RT for 16 h
  2. washThe Organics were washed with H2O (3×500 mL), brine (500 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-9bd626399564456e8b688e1f7d4f3ddb
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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