Triethylamine → 3-{5-(4-methyl-benzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene

HRID 369395Notes

Reaction equation

HRID 369395 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:12][CH:13]=1.[CH3:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.C(N(CC)CC)C>>[CH3:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([C:6]2[N:2]([CH3:1])[C:3]([CH2:7][C:8]3[CH:9]=[C:10]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:5]=2)=[O:23])=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 232857013-(1-Methylpyrrol-2-ylmethyl)nitrobenzene

Product 1

HCID 539054163-{5-(4-methyl-benzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzeneYield 28%

Procedure

3-(1-Methylpyrrol-2-ylmethyl)nitrobenzene (2.0 g, 9.2 mmol) [prepared as in Example 8, Step (b)], 4-methylbenzoyl chloride (2.84 g, 18.4 mmol), and triethylamine (2.0 ml, 14.3 mmol) were dissolved in xylenes (80 ml) and the reaction mixture was refluxed for 36 h. Purification on a Florisil column (hexane-ethyl acetate, 95:5) gave 3-{5-(4-methyl-benzoyl)-1-methyl-1H-pyrrol-2-ylmethyl}nitrobenzene (0.86 g, 28%) as a solid. ##STR45##

Workup

  1. temperaturethe reaction mixture was refluxed for 36 h
  2. customPurification on a Florisil column (hexane-ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-37314d1b700049b2954fcc4c9e77fe4d
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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