Imidazole → HCID 89154806, compound

HRID 2170728Notes

Reaction equation

HRID 2170728 reaction equation
N1[CH:5]=[CH:4]N=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[C:14]1(/[CH:42]=[CH:43]/[C:44]2[CH:49]=[CH:48][C:47]([CH2:50][CH:51]([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([Br:63])=[CH:59][CH:58]=3)[C:52]([CH3:55])([OH:54])[CH3:53])=[CH:46][CH:45]=2)[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH2:34][C:35]3[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=3)[C:30]([CH3:33])([OH:32])[CH3:31])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:63][C:60]1[CH:59]=[CH:58][C:57]([CH2:56][CH:51]([C:52]([CH3:53])([O:54][Si:8]([CH2:4][CH3:5])([CH2:9][CH3:10])[CH2:6][CH3:7])[CH3:55])[CH2:50][C:47]2[CH:46]=[CH:45][C:44](/[CH:43]=[CH:42]/[C:14]3[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]4[CH:23]=[CH:24][C:25]([CH2:28][CH:29]([CH2:34][C:35]5[CH:40]=[CH:39][C:38]([Br:41])=[CH:37][CH:36]=5)[C:30]([O:32][Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:6][CH3:7])([CH3:33])[CH3:31])=[CH:26][CH:27]=4)=[CH:16][CH:15]=3)=[CH:49][CH:48]=2)=[CH:62][CH:61]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 25517Ammonium ChlorideHCID 89177694HCID 89177694, compound

Product 1

HCID 89154806HCID 89154806, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (136 mg, 2.0 mmol), triethylsilyl chloride (0.25 mL, 3.0 mmol) and N,N-dimethylformamide (2.50 mL) were added at 0° C. to 4,4′-((1E,1′E)-1,4-phenylenebis(ethen-2,1-diyl)bis(4,1-phenylene))bis(3-(4-bromobenzyl)-2-methylbutan-2-ol) (396 mg, 0.50 mmol). Following stirring of the resulting mixed liquid at room temperature for 12 hours, a saturated aqueous solution of ammonium chloride was added to halt the reaction. The organic layer was separated from the mixed liquid, and the water layer was extracted with ether. The resulting organic layer was washed with water, dried using anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane), yielding the title compound (10b) (444 mg, 0.43 mmol) as a yellow viscous solid in a yield of 87%.

Workup

  1. additionmixed liquid at room temperature for 12 hours
  2. customthe reaction
  3. customThe organic layer was separated from the mixed liquid
  4. extractionthe water layer was extracted with ether
  5. washThe resulting organic layer was washed with water
  6. customdried
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-33c8945aecd349efa79f77c134f6395c
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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