Imidazole → HCID 22713511, compound

HRID 351855Notes

Reaction equation

HRID 351855 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1.[C:14]([Si:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)Cl)([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[C:14]([Si:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[O:1][C:2]1[CH:13]=[CH:12][C:5]2[NH:6][C:7](=[O:11])[O:8][C:9](=[O:10])[C:4]=2[CH:3]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 22713511HCID 22713511, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Hydroxy-1H-benzo[d][1,3]oxazine-2,4-dione (9.7 g, 54 mmol), tert-butyldiphenylchlorosilane (15.2 mL, 59 mmol) and imidazole (4 g, 59 mmol) were stirred in DMF (100 mL) for 24 h at rt. The reaction mixture was extracted with ethyl acetate (400 mL) and water 300 mL). The product in the organic layer was purified by chromatography on silica gel in hexane/ethyl acetate 2:1 and then crystallized from hot ethyl acetate/hexane, affording white crystals (13 g, 58%), mp. 185° C.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (400 mL) and water 300 mL)
  2. customThe product in the organic layer was purified by chromatography on silica gel in hexane/ethyl acetate 2:1
  3. customcrystallized from hot ethyl acetate/hexane

Sources & evidence

ORD record
ord-7b0ed0ff146447debdfa71a9bd645638
Source dataset
uspto-grants-2004_06
Patent number
US06743789B2

Reaction notes

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