Imidazole → HCID 18987804, compound

HRID 2396589Notes

Reaction equation

HRID 2396589 reaction equation
[Si:1](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:24][CH:25]([CH2:28][CH3:29])[CH2:26][OH:27]>CCCCCC>[Si:1]([O:27][CH2:26][CH:25]([CH3:24])[CH2:28][CH3:29])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 87232-Methyl-1-butanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 18987804HCID 18987804, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a small pressure-equalizing addition funnel, a thermocouple connected to a THERM-O-WATCH®, a reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 46.27 grams (0.168 mole, 1.01 equivalents) of t-butyldiphenylsilyl chloride, 11.69 grams (0.172 mole, 1.03 equivalents) of imidazole, and 100 mls of hexane. 2-Methyl-1-butanol, 14.69 grams (0.167 mole, 1.00 equivalent), was then added dropwise to the resultant slurry. A very mild exotherm was detected. The total feed time was twelve minutes. A fine white precipitate formed almost immediately. The reaction mixture was stirred at room temperature, and monitored by GC analysis. An aliquot of the clear supernatant was injected into the GC. After seven hours, both starting materials were still present. Therefore, the reaction mixture was heated to 60° C. with a heating mantle, controlled by the THERM-O-WATCH®. The reaction mixture was stirred overnight at 60° C. The sample after 23.5 hours indicated all the starting material had been consumed, with the formation of a single, higher boiling component. The reaction mixture was allowed to cool to room temperature, then it was transferred to a small, dry, Chemglass pressure filter. The filtrate was collected in a dry, 500 ml flask. The filter cake was rinsed with additional hexane (2×100 ml). The solvent was removed on the rotary evaporator, with the bath temperature set at 40° C.

Workup

  1. customA 250 ml, three-necked flask was fitted with a large magnetic,
  2. additionegg-shaped stir bar, a small pressure-equalizing addition funnel
  3. customThis apparatus was dried in an oven overnight at 125° C.
  4. waitThe total feed time was twelve minutes
  5. customA fine white precipitate formed almost immediately
  6. temperatureTherefore, the reaction mixture was heated to 60° C. with a heating mantle
  7. stirringThe reaction mixture was stirred overnight at 60° C
  8. waitThe sample after 23.5 hours indicated
  9. customall the starting material had been consumed, with the formation of a single,
  10. temperatureto cool to room temperature
  11. customdry
  12. filtrationChemglass pressure filter
  13. customThe filtrate was collected in a dry, 500 ml flask
  14. washThe filter cake was rinsed with additional hexane (2×100 ml)
  15. customThe solvent was removed on the rotary evaporator, with the bath temperature
  16. customset at 40° C.

Sources & evidence

ORD record
ord-080c94d83b1242c28f33fb024f3d06c2
Source dataset
uspto-grants-1996_02
Patent number
US05493044

Reaction notes

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