Imidazole → HCID 70976304, compound

HRID 2170729Notes

Reaction equation

HRID 2170729 reaction equation
N1C=CN=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[Br:14][C:15]1[S:19][C:18]([C:20]2[CH:44]=[CH:43][C:23]([CH2:24][CH:25]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([C:37]4[S:38][C:39]([Br:42])=[CH:40][CH:41]=4)=[CH:33][CH:32]=3)[C:26]([CH3:29])([OH:28])[CH3:27])=[CH:22][CH:21]=2)=[CH:17][CH:16]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:42][C:39]1[S:38][C:37]([C:34]2[CH:33]=[CH:32][C:31]([CH2:30][CH:25]([CH2:24][C:23]3[CH:43]=[CH:44][C:20]([C:18]4[S:19][C:15]([Br:14])=[CH:16][CH:17]=4)=[CH:21][CH:22]=3)[C:26]([O:28][Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[CH2:6][CH3:7])([CH3:27])[CH3:29])=[CH:36][CH:35]=2)=[CH:41][CH:40]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 25517Ammonium ChlorideHCID 68272395HCID 68272395, compound

Product 1

HCID 70976304HCID 70976304, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole (245 mg, 3.6 mmol), triethylsilyl chloride (1.2 mL, 7.2 mmol) and N,N-dimethylformamide (10 mL) were added at 0° C. to 3-(4-(5-bromothiophen-2-yl)benzyl)-4-(4-(5-bromothiophen-2-yl)phenyl)-2-methylbutan-2-ol (1.15 g, 2.0 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 a saturated aqueous solution of sodium chloride, and dried using anhydrous magnesium sulfate. Following filtering of the organic layer, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane), yielding the title compound (7b) (1.35 g, 1.95 mmol) as a colorless solid in a yield of 98%.

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 a saturated aqueous solution of sodium chloride
  6. customdried
  7. filtrationFollowing filtering of the organic layer
  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-b15b9fd200ea4bba8170b8f34219a3aa
Source dataset
uspto-grants-2015_06
Patent number
US09051246B2

Reaction notes

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