2,6-Di-tert-butyl-4-methylphenol → N-(3-Ethyl-4-nitrophenyl)-2-methyloxirane-2-carboxamide

HRID 133781Notes

Reaction equation

HRID 133781 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:14]1[CH:15]=[C:16]([NH:23][C:24](=[O:28])[C:25]([CH3:27])=[CH2:26])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH3:13].C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C>ClCCl>[CH2:12]([C:14]1[CH:15]=[C:16]([NH:23][C:24]([C:25]2([CH3:27])[CH2:26][O:6]2)=[O:28])[CH:17]=[CH:18][C:19]=1[N+:20]([O-:22])=[O:21])[CH3:13]

Participants

5

Reactant 3

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 70297m-Chloroperbenzoic acidHCID 67526083N-(3-Ethyl-4-nitrophenyl)-2-methylprop-2-enamide

Product 1

HCID 71419999N-(3-Ethyl-4-nitrophenyl)-2-methyloxirane-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (14.71 g, 0.08524 mol) was added in portions to the refluxing solution of N-(3-ethyl-4-nitrophenyl)-2-methylacrylamide (6.68 g, 0.02852 mol) and 2,6-di-tert-butyl-4-methylphenol (149 mg) in dichloromethane (180 ml). After refluxing for 5 h the reaction mixture was allowed to cool to room temperature. The precipitated 3-chlorobenzoic acid was filtered, and the filtrate was extracted three times with 1M Na2CO3 and water. The organic phase was dried over Na2SO4, filtered and evaporated. The crude product was purified by flash chromatography using dichloromethane as an eluent. 1H NMR (400 MHz, DMSO-d6): 1.20 (3H, t, 3J=7.4 Hz), 1.55 (3H, s), 2.84 (2H, q, 3J=7.4 Hz), 2.99 (1H, d, 2Jgem=5.1 Hz), 3.06 (1H, d, 2Jgem=5.1 Hz), 7.81 (1H, dd, 3J=9.0 Hz, 4J=2.3 Hz), 7.85 (1H, d, 4J=2.2 Hz), 7.97 (1H, d, 3J=9.0 Hz), 9.88 (1H, s, —NHCO—).

Workup

  1. temperatureAfter refluxing for 5 h the reaction mixture
  2. filtrationThe precipitated 3-chlorobenzoic acid was filtered
  3. extractionthe filtrate was extracted three times with 1M Na2CO3 and water
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-b362a8b245b54b77b5fe3aab30308b0f
Source dataset
uspto-grants-2008_06
Patent number
US07390923B2

Reaction notes

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