Acetic Anhydride → 5-acetamido-N-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxybenzamide

HRID 1777406Notes

Reaction equation

HRID 1777406 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1)=[O:8].[C:26](OC(=O)C)(=[O:28])[CH3:27]>CC(O)=O>[C:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH:24]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)=[O:8])(=[O:28])[CH3:27]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 10406441HCID 10406441, compound

Product 1

HCID 715548855-acetamido-N-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxybenzamideYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5-Amino-N-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxybenzamide (364.24 mg, 1 mmol) obtained in Example 31 was dissolved in acetic anhydride (0.09 ., 1 mmol), to which AcOH (3 ml) was added, followed by stirring at room temperature for 3 hours. The mixture was extracted by using ethylacetate. The extract was washed with saturated sodium hydrogen carbonate, and dried over MgSO4. After eliminating ethylacetate, the non-purified compound was purified by silica gel column chromatography (ethylacetate:hexane=1:1) to give 340 mg of the target compound (yield: 84%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted
  3. washThe extract was washed with saturated sodium hydrogen carbonate
  4. dry with materialdried over MgSO4
  5. customthe non-purified compound was purified by silica gel column chromatography (ethylacetate:hexane=1:1)

Sources & evidence

ORD record
ord-ea5e236c4f6d4a10b5a25db5ead42ea9
Source dataset
uspto-grants-2016_02
Patent number
US09266872B2

Reaction notes

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