1,2-Dichloroethane → HCID 22181326, compound

HRID 1796509Notes

Reaction equation

HRID 1796509 reaction equation
ClCCCl.CC#N.C(OC1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:20][C:21]2[CH:26]=[C:25]([NH:27][CH3:28])[CH:24]=[CH:23][C:22]=2[N+:29]([O-:31])=[O:30])=[O:19])=[CH:13]C=1)C.[C:32](Cl)(=[O:37])[CH2:33][CH:34]([CH3:36])[CH3:35].[CH3:39][CH2:40][O:41][CH2:42][CH3:43]>CN(C1C=CN=CC=1)C>[CH2:40]([O:41][C:42]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([NH:20][C:21]2[CH:26]=[C:25]([N:27]([CH3:28])[C:32](=[O:37])[CH2:33][CH:34]([CH3:36])[CH3:35])[CH:24]=[CH:23][C:22]=2[N+:29]([O-:31])=[O:30])=[O:19])=[CH:13][CH:43]=1)[CH3:39]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 66054Isovaleryl chlorideHCID 22181284HCID 22181284, compound

Product 1

HCID 22181326HCID 22181326, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a 1:1/DCE:CH3CN solution (50 mL) of 4-ethoxy-N-[5-(methylamino)-2-nitrophenyl]-benzeneacetamide (845 mg, 2.56 mmol) and DMAP (470 mg, 1.5 eq) was added isovaleryl chloride (0.47 mL, 1.5 eq). The solution was stirred at rt for 48 h. The solution was then washed with 5% KHSO4, saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 7:1/CH2Cl2:ether to give the desired product 4-ethoxy-N-[5-[methyl(3-methyl-1-oxobutyl)amino]-2-nitrophenyl]-benzeneacetamide (1.06 g, 99% yield); 1H NMR (400 MHz, CDCl3) δ 8.72 (s, 1H), 8.21 (d, J=8.8 Hz, 1H), 7.26 (m, 3H), 6.96 (m, 2H), 4.06 (m, 2H), 3.76 (s, 2H), 3.31 (s, 3H), 2.15 (m, 3H), 1.42 (t, J=7.2 Hz, 3H), 0.88 (d, J=6.8 Hz, 6H).

Workup

  1. washThe solution was then washed with 5% KHSO4, saturated NaHCO3 solution, brine
  2. dry with materialdried over anhydrous MgSO4
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-baba4ac2c4824c2695d98b6456ad4f67
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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