Imidazole → HCID 131734478, compound

HRID 590404Notes

Reaction equation

HRID 590404 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].N1C=CN=[CH:12]1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17].[OH2:34]>CN(C=O)C.CCOCC.C(Cl)Cl>[Si:20]([O:34][CH2:12][C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:10])[O:1][C:5]=2[CH:6]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 60432(3H)-Benzoxazolone2×HCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 131734478HCID 131734478, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-hydroxymethyl)-1,3-benzoxazol-2(3H)-one (Intermediate 77, 330 mg, 2.0 mmol) in DMF (10 mL) was added imidazole (203 mg, 2.98 mmol) and the reaction was cooled to 0° C. before tert-butylchlorodiphenylsilane (0.52 mL, 2.0 mmol) was added dropwise. Upon addition, the reaction was allowed to warm up to room temperature and stirring was maintained for 16 hours. Water and CH2Cl2 (40 mL each) were added to the reaction mixture and the phases were separated. The aqueous phase was extracted with CH2Cl2 (2×50 mL) and the resulting organic extracts were washed with water (2×50 mL) and brine (50 mL), dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure. The brown oil obtained was purified by column chromatography over silica gel eluting with Hexane:Et2O (from 0 to 100% of Et2O) to afford the title compound as a beige solid (437 mg, 54% yield).

Workup

  1. additionwas added dropwise
  2. additionUpon addition
  3. temperaturewas maintained for 16 hours
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  6. washthe resulting organic extracts were washed with water (2×50 mL) and brine (50 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe brown oil obtained
  11. customwas purified by column chromatography over silica gel eluting with Hexane

Sources & evidence

ORD record
ord-ca4803a9a29247228567d00453d00a24
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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