Toluene → HCID 86605605, compound

HRID 1796508Notes

Reaction equation

HRID 1796508 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:10]=[C:11]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37](Cl)=[O:38])=[CH:32][CH:31]=1)[CH3:28]>[Zn].CCOC(C)=O>[CH2:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([NH:8][C:9]2[CH:10]=[C:11]([CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH:12]=[CH:13][C:14]=2[N+:15]([O-:17])=[O:16])=[O:38])=[CH:32][CH:31]=1)[CH3:28]

Participants

6

Reactant 3

HCID 1140TolueneHCID 116297822-(4-ethoxyphenyl)acetyl ChlorideHCID 86605604HCID 86605604, compound

Product 1

HCID 86605605HCID 86605605, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring toluene solution (100 mL) of (3-Amino-4-nitrophenyl)methyl-carbamic acid, 1,1-dimethylethyl ester (1.10 g, 4.12 mmol) were added 4-ethoxyphenylacetyl chloride (980 mg, 1.2 eq) and zinc dust (400 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 was 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 2:1/hex:EtOAc on silica gel to yield the desired product [3-[[(4-Ethoxyphenyl)acetyl]amino]-4-nitrophenyl]methyl-carbamic acid, 1,1-dimethylethyl ester (1.18 g, 67% yield); 1H NMR (400 MHz, CDCl3) δ 8.77 (s, 1H), 8.11 (d, J=9.2 Hz, 1H), 7.22 (m, 3H), 6.93 (d, J=9.2 Hz, 2H), 4.40 (m, 2H), 3.75 (s, 2H), 3.33 (s, 3H), 1.50 (s, 9H), 1.42 (t, J=6.8 Hz, 3H).

Workup

  1. stirringthe solution was 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-8c866f6ca84041ea83989e8f28d0ac0c
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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