Imidazole → 5-chloro-6-[(triisopropylsilyl)oxy]-1,3-benzoxazol-2(3H)-one

HRID 270130Notes

Reaction equation

HRID 270130 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:18]([CH3:20])[CH3:19])=[CH:4][C:5]2[O:9][C:8](=[O:10])[NH:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 27346-HydroxychlorzoxazoneHCID 139400Triisopropylsilyl chloride

Product 1

HCID 689628865-chloro-6-[(triisopropylsilyl)oxy]-1,3-benzoxazol-2(3H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-chloro-6-hydroxy-1,3-benzoxazol-2(3H)-one (0.93 g, 5 mmol) and imidazole (1.00 g, 15 mmol) were dissolved in dimethylformamide (10 mL) with stirring under inert atmosphere. Triisopropylsilylchloride (1.15 g, 6 mmol) was added and the resulting solution was stirred for 3 days. The reaction mixture was partitioned between water and heptane. The organic layer was washed with water and dried over magnesium sulphate, filtrated and concentrated, to give 1.45 g (85%) of the subtitled compound as a grey solid.

Workup

  1. stirringthe resulting solution was stirred for 3 days
  2. customThe reaction mixture was partitioned between water and heptane
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c79150d587fc43059eb8de52887fbb0e
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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