Water → HCID 22632985, compound

HRID 2416857Notes

Reaction equation

HRID 2416857 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-c6791a600ae74eb8802b8568b078c6ae
Source dataset
uspto-grants-2004_11
Patent number
US06825199B2

Reaction notes

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