Sodium hydride → HCID 178455036, compound

HRID 1848903Notes

Reaction equation

HRID 1848903 reaction equation
[OH:1][C:2]1[C:10]2[N:9]=[N:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:13]([Si:17]([CH3:20])([CH3:19])Cl)([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+]>O1CCCC1>[C:13]([Si:17]([CH3:20])([CH3:19])[O:1][C:2]1[C:10]2[N:9]=[N:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chloride2×HCID 178418300HCID 178418300, compound

Product 1

HCID 178455036HCID 178455036, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-hydroxybenzotriazole (5.000 g) in tetrahydrofuran (250 mL) was added sodium hydride (60%, 0.932 g). The solution was stirred at room temperature for 20 minutes, cooled to 0° C., tert-butyldimethylchlorosilane (5.860 g) was added, the solution was allowed to warm to room temperature, and stirred for 16 hours. Additional sodium hydride (60%, 0.500 g) was added, the solution stirred for 15 minutes, additional tert-butyldimethylchlorosilane (3.000 g) was added, and the solution stirred for three hours at room temperature. The solution was then added to saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography on silica gel using 20-30% ethyl acetate in hexanes.

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 16 hours
  4. stirringthe solution stirred for 15 minutes
  5. stirringthe solution stirred for three hours at room temperature
  6. extractionextracted with ethyl acetate
  7. extractionThe organic extract
  8. washwas washed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. custompurified by flash column chromatography on silica gel using 20-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f0ea7dfbdabc4e75ba28e8c6e273a10f
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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