Dimethyl Sulfoxide → HCID 58058451, compound

HRID 1873938Notes

Reaction equation

[CH3:1][C:2]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:29])([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)([CH2:4][C:5]([CH3:8])([CH3:7])[CH3:6])[CH3:3].F[C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1.[H-].[Na+].CS(C)=O>CO>[N+:37]([C:34]1[CH:35]=[CH:36][C:31]([N:15]([C:12]2[CH:13]=[CH:14][C:9]([C:2]([CH3:1])([CH2:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH3:3])=[CH:10][CH:11]=2)[C:16]2[CH:17]=[CH:18][C:19]([C:22]([CH3:29])([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH3:23])=[CH:20][CH:21]=2)=[CH:32][CH:33]=1)([O-:39])=[O:38]

Participants

Conditions

Temperature: 120 °C

Procedure

First, 76.20 mmol of Bis-(4-(2,4,4-trimethylpentan-2-yl)phenyl)amine, 91.45 mmol of 4-Fluoronitrobenzene, 114.31 mmol of sodium hydride, 2.74 g of NaH, and 120 ml of dimethyl sulfoxide (DMSO) were added into a bottle. After stirring at 120° C. for 48 hrs, the reaction mixture was cooled and then poured into 1 L of methanol. The yellow precipitate was collected by filtration and dried under vacuum. The product was purified by silica gel column chromatography (dichloromethane:n-hexane=1:3) and recrystallized from ethyl acetate to afford 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline as a yellow crystal with a yield of 60%. The 4-nitro-N,N-bis(4-(2,4,4-trimethylpentan-2-yl)phenyl)aniline had a melt point of 167° C. The synthesis pathway was as follows:

Workup

temperaturethe reaction mixture was cooled
filtrationThe yellow precipitate was collected by filtration
customdried under vacuum
customThe product was purified by silica gel column chromatography (dichloromethane:n-hexane=1:3)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-6d3b6b8bfcfc45d787fdb7bfdb16d369
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304514B2

Reaction notes

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