Toluene → N-[5-[(Diethylamino)carbonyl]-2-nitrophenyl]-4-ethoxy-benzeneacetamide

HRID 1796504Notes

Reaction equation

HRID 1796504 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:10]=[C:11]([CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[C:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])=[O:13].[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][C:35](Cl)=[O:36])=[CH:30][CH:29]=1)[CH3:26]>[Zn].CCOC(C)=O>[CH2:17]([N:14]([CH2:15][CH3:16])[C:12]([C:11]1[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:9]([NH:8][C:35](=[O:36])[CH2:34][C:31]2[CH:32]=[CH:33][C:28]([O:27][CH2:25][CH3:26])=[CH:29][CH:30]=2)[CH:10]=1)=[O:13])[CH3:18]

Participants

6

Reactant 3

HCID 1140TolueneHCID 116297822-(4-ethoxyphenyl)acetyl ChlorideHCID 221814143-Amino-N,N-diethyl-4-nitrobenzamide

Product 1

HCID 22181377N-[5-[(Diethylamino)carbonyl]-2-nitrophenyl]-4-ethoxy-benzeneacetamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring toluene solution (100 mL) of 3-amino-N,N-diethyl-4-nitro-benzamide (1.00 g, 4.21 mmol) were added 4-ethoxyphenylacetyl chloride (1.25 g, 1.5 eq) and zinc dust (415 mg, 1.5 eq). The solution was stirred at rt overnight. Another 0.5 eq of acid chloride and zinc dust were then added and the solution stirred at rt for another 24 h. The solution was then filtered through celite and rinsed with EtOAc. The organic phase was washed with saturated NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by flash chromatography using 1:1/hex:EtOAc on silica gel to furnish the desired product (1.52 g, 90% yield). 1H NMR (400 MHz, CDCl3) d 8.81 (s, 1H), 8.20 (d, J=8.8 Hz, 1H), 7.26 (m, 3H), 7.15 (d, J=8.8 Hz, 1H), 6.94 (d, J=8.4 Hz, 2H), 4.06 (q, J=7.2 Hz, 2H), 3.75 (s, 2H), 3.54 (q, J=6.8 Hz, 2H), 3.24 (q, J=6.8 Hz, 2H), 1.59 (br s, 1H), 1.42 (t, J=6.8 Hz, 3H), 1.25 (t, J=6.8 Hz, 3H), 1.16 (t, J=6.8 Hz, 3H).

Workup

  1. stirringthe solution stirred at rt for another 24 h
  2. filtrationThe solution was then filtered through celite
  3. washrinsed with EtOAc
  4. washThe organic phase was washed with saturated NaHCO3 solution, brine
  5. dry with materialdried over anhydrous MgSO4
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e828a44b758b4b78ba0f69850e2a85a0
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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