Toluene → HCID 22632960, compound

HRID 2270191Notes

Reaction equation

HRID 2270191 reaction equation
[C:1](Cl)(Cl)=[O:2].C1(C)C=CC=CC=1.[OH:12][C:13]1[CH:38]=[CH:37][C:16]([NH:17][C:18]2[CH:34]=[C:33]([F:35])[C:32]([F:36])=[CH:31][C:19]=2[C:20]([NH:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:21])=[CH:15][CH:14]=1>O1CCOCC1>[OH:12][C:13]1[CH:38]=[CH:37][C:16]([N:17]2[C:18]3[C:19](=[CH:31][C:32]([F:36])=[C:33]([F:35])[CH:34]=3)[C:20](=[O:21])[N:22]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:1]2=[O:2])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6371PhosgeneHCID 22633005HCID 22633005, compound

Product 1

HCID 22632960HCID 22632960, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A 2N solution of phosgene in toluene (2.5 mL, 5 mmol) was added to a solution of crude 2-(4-hydroxyanilino)-N-benzyloxy-4,5-difluoro-benzamide (Example I-1, 0.35 g, 0.95 mmol) in 20 mL of dioxane. The solution was heated at reflux for 2 hours, cooled down to room temperature and poured into ice water, and extracted with ethyl acetate (3×30 mL). Combined extracts were washed with water, brine, and dried over sodium sulfate to give 0.065 g of the title product as a solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 2 hours
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washCombined extracts were washed with water, brine
  5. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-53f19ca39d5f473283ad6903f9765318
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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