Water → HCID 22632985, compound

HRID 2270247Notes

Reaction equation

HRID 2270247 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[NH2:12][C:13]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:14]=1[C:15]([NH:17][O:18][CH2:19][CH:20]=[CH2:21])=[O:16].O>O1CCOCC1>[CH2:19]([O:18][N:17]1[C:15](=[O:16])[C:14]2[C:13](=[CH:25][C:24]([F:26])=[C:23]([F:27])[CH:22]=2)[NH:12][C:1]1=[O:2])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6371PhosgeneHCID 22633003HCID 22633003, compound

Product 1

HCID 22632985HCID 22632985, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phosgene, as a 12.5% solution in toluene (9.4 mL, 12 mmol), was added to a solution of 2-amino-N-allyloxy-4,5-difluorobenzamide (Example Y-3, 2.08 g, 9.1 mmol) in 75 mL of dioxane. The solution was heated at reflux for 20 hours and then poured into 200 mL of water. The aqueous solution was extracted with ethyl acetate, and the combined organic fractions were washed with water and brine and dried over magnesium sulfate. The solution was concentrated to give 2.18 g of the title compound as a solid, mp 220-221° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 20 hours
  3. extractionThe aqueous solution was extracted with ethyl acetate
  4. washthe combined organic fractions were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-b1d20b5a7acf4b568552aeab20ce8e06
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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