Butanedione → 2,3-Bis(2,5-bis(4-tert-butylphenyl)-pyrrol-1-ylimino)-butane

HRID 1265292Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([NH2:26])[C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=3)=[CH:14][CH:15]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28](=O)[C:29](=O)[CH3:30].[C:33]1([CH3:43])[CH:38]=[CH:37][C:36](S(O)(=O)=O)=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:13]2[N:12]([N:26]=[C:28]([C:29](=[N:26][N:12]3[C:43]([C:33]4[CH:38]=[CH:37][C:36]([C:16]([CH3:21])([CH3:17])[CH3:13])=[CH:35][CH:34]=4)=[CH:14][CH:15]=[C:11]3[C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[CH3:30])[CH3:27])[C:11]([C:8]3[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][CH:9]=3)=[CH:15][CH:14]=2)=[CH:21][CH:20]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2,5-bis-(4-tert-butyl-phenyl)-pyrrol-1-ylamine (174 mg, 0.502 mmol) in toluene (4.5 mL) was treated with butanedione (19.7 μL, 0.225 mmol) and p-toluene sulfonic acid (5.2 mg). The resulting solution was heated to 80° C. in an oil bath under Ar overnight. The solution was cooled to rt and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 33% CH2Cl2/heptane) to afford 2,3-bis(2,5-bis(4-tert-butylphenyl)-pyrrol-1-ylimino)-butane (121 mg, 72%): 1H NMR (CDCl3, chemical shifts in ppm relative to TMS): 1.33 (s, 36H), 1.69 (s, 6H), 6.39 (s, 4H), 7.33-7.39 (m, 16H).

Workup

temperatureThe solution was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (SiO2, 33% CH2Cl2/heptane)

Sources & evidence

ORD record: ord-be23cc70441f483d8f838a7a4f0ff2ba
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545108B1

Reaction notes

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