Propanedioyl dichloride → 2-(2,4-Dioxo-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamide

HRID 343116

Reaction equation

HRID 343116 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11].[C:22](Cl)(=[O:27])[CH2:23][C:24](Cl)=[O:25]>C1COCC1>[O:25]=[C:24]1[N:8]([CH2:9][C:10]([N:12]([CH:19]([CH3:21])[CH3:20])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:11])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:22](=[O:27])[CH2:23]1

Participants

4

Reactant 2

HCID 74269Propanedioyl dichlorideHCID 541932642-(2-Aminophenylamino)-N-isopropyl-N-phenyl acetamide

Product 1

HCID 867535892-(2,4-Dioxo-2,3,4,5-tetrahydro benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl acetamideYield 46.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 10 g (37.14 mmol) of 2-(2-Aminophenylamino)-N-isopropyl-N-phenyl acetamide, prepared as in Intermediate 45, in 100 mL of THF is added 5.2 g (37.14 mmol, 1 equiv.) of malonyl dichloride. The resulting solution is stirred at RT for 2 h and the solvent removed in vacuo. Purification by silica gel flash column chromatography using hexane/EtOAc 1/1 as eluent afforded 6.1 g of the title compound as an oil: 1H NMR (CDCl3, 300 MHz) δ9.65 (s, 1H), 7.4 (bd, 1H, J=9), 7.30-6.93 (m, 7H), 5.09-4.95 (m, 1H), 4.42 (d, 1H, J=16), 3.68 (d, 1H, J=17), 3.36 (d, 2H, J=4), 1.09 (d, 6H, J=7).

Workup

  1. customthe solvent removed in vacuo
  2. customPurification by silica gel flash column chromatography

Sources & evidence

ORD record
ord-b072cba231b84573992b05c04663df44
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Linked notes

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