Water → HCID 15908875, compound

HRID 2270160Notes

Reaction equation

HRID 2270160 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[NH2:12][C:13]1[CH:29]=[C:28]([F:30])[C:27]([F:31])=[CH:26][C:14]=1[C:15]([NH:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:16].O>O1CCOCC1>[CH2:19]([O:18][N:17]1[C:15](=[O:16])[C:14]2[C:13](=[CH:29][C:28]([F:30])=[C:27]([F:31])[CH:26]=2)[NH:12][C:1]1=[O:2])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 6371PhosgeneHCID 15908874HCID 15908874, compound

Product 1

HCID 15908875HCID 15908875, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phosgene, 12.5% solution in toluene, (16 mL, 20 mmol) was added to a solution of 2-amino-N-benzyloxy-4,5-difluoro-benzamide (Example A, 5.54 g, 19.9 mmol) in 160 mL of dioxane. The solution was heated at reflux for 5 hours and then poured into 450 mL of water. The aqueous solution was extracted with ethyl acetate; the combined organic extracts were washed with water, brine, and dried over magnesium sulfate. The solution was concentrated to give 5.73 g of the title compound as a solid, mp>250° C.

Workup

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

Sources & evidence

ORD record
ord-c71dadcba2d743d083d0e8dfe02e4e7e
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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