Imidazole → 6-(tert-Butyl-dimethyl-silanyloxy)-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 395727Notes

Reaction equation

HRID 395727 reaction equation
[OH:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O.O>[Si:19]([O:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 27593156-hydroxy-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Product 1

HCID 116808836-(tert-Butyl-dimethyl-silanyloxy)-1H-benzo[d][1,3]oxazine-2,4-dioneYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-hydroxyisatoic anhydride (1.6 g, 9.0 mmol) and imidazole (670 mg, 9.9 mmol) in N,N-dimethylformamide (10 mL) was added tert-butyldimethylsilyl chloride N (1.42 g, 9.45 mmol). After stirring for 2 h, the reaction mixture was diluted with ice and water. After warming to room temperature, the resulting precipitate was filtered and washed with water and hexane. The solid was vacuum dried at 55° C./0.1 mm for 14 h to give 2.55 g (96%) of the title compound as a light gray solid; mp 198-200° C. (dec).

Workup

  1. filtrationthe resulting precipitate was filtered
  2. washwashed with water and hexane
  3. customdried at 55° C./0.1 mm for 14 h

Sources & evidence

ORD record
ord-9f182989fc574dd286cb255e9a8dda4e
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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