Triethylamine → 4-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene

HRID 618325Notes

Reaction equation

HRID 618325 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.[CH3:17][C:18]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:19]=1[C:20](Cl)=[O:21].C(N(CC)CC)C.[O-][Si]([O-])=O.[Mg+2]>CCCCCC.C(OCC)(=O)C.CCCCCC>[CH3:17][C:18]1[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:19]=1[C:20]([C:6]1[N:2]([CH3:1])[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:5]=1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 61680MAGNESIUM SILICATE (synthetic)HCID 1408672,4-Dimethylbenzoyl chlorideHCID 232857944-(1-Methylpyrrol-2-ylmethyl)nitrobenzene

Product 1

HCID 232857664-{5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzeneYield 42.3%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-(1-Methylpyrrol-2-ylmethyl)nitrobenzene (1.2 g, 5.5 mmol) [prepared as in Example 7, Step (b)], 2,4-dimethylbenzoyl chloride (1.6 g, 9.5 mmol), and triethylamine (1.3 ml, 9.3 mmol) were dissolved in xylenes (50 ml), and the reaction mixture was heated at reflux under argon. After 48 h, the reaction mixture was passed through a Florisil® column (hexane followed by hexane-ethyl acetate, 95:5) to give 4-(5-(2,4-dimethylbenzoyl)-1-methyl-1H-pyrrol-2-yl-methyl)nitrobenzene (0.81 g, 42%) as a solid. ##STR41##

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux under argon

Sources & evidence

ORD record
ord-9796ddaf2c7f4e768e839fb292468925
Source dataset
uspto-grants-1999_09
Patent number
US05952368

Reaction notes

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