Sodium Hydroxide → HCID 19907336, compound

HRID 2371448Notes

Reaction equation

HRID 2371448 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]2[C:6](=[O:11])[O:7][C:8](=O)[NH:9][C:4]=2[CH:3]=1.[OH-].[Na+].[CH3:16][Si:17]([CH3:22])([CH3:21])[CH2:18]CO>C(OC(C)C)(C)C>[F:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5](=[CH:12][CH:13]=1)[C:6]([O:7][CH2:8][CH2:16][Si:17]([CH3:22])([CH3:21])[CH3:18])=[O:11]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 180132-(Trimethylsilyl)ethanolHCID 100581387-Fluoroisatoic anhydride

Product 1

HCID 19907336HCID 19907336, compound

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

7-Fluoro-1H-3,1-benzoxazine-2,4-dione (2.0 g), sodium hydroxide (0.05 g) and 2-(trimethylsilyl)ethanol (1.31 g) were heated together at 100° for 30 minutes until effervescence ceased. After cooling, the residue was suspended in diisopropyl ether, then filtered and evaporated. The residue was recrystallised from petroleum ether to give 2-(trimethylsilyl)ethyl 4-fluoroanthranilate, mp 43°-44°. (Compound 20).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. customevaporated
  4. customThe residue was recrystallised from petroleum ether

Sources & evidence

ORD record
ord-e8c7d98d6a2e4adcaa4b3eff9f08eac1
Source dataset
uspto-grants-1992_03
Patent number
US05093364

Reaction notes

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