Acetic Anhydride → 4-(acetamidomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methyl-phenyl]benzamide

HRID 587835Notes

Reaction equation

HRID 587835 reaction equation
[NH2:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18]([F:21])([F:20])[F:19])=[CH:12][C:11]=2[CH2:27][CH3:28])=[O:8])=[CH:5][CH:4]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>O1CCCC1.O>[C:31]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([C:17]([F:26])([C:18]([F:19])([F:20])[F:21])[C:22]([F:23])([F:24])[F:25])=[CH:12][C:11]=2[CH2:27][CH3:28])=[O:8])=[CH:29][CH:30]=1)(=[O:33])[CH3:32]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 866666174-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]benzamide

Product 1

HCID 866666184-(acetamidomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methyl-phenyl]benzamideYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude product of 4-(aminomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoro-propan-2-yl)-6-methylphenyl]benzamide (0.30 g) was dissolved in tetrahydrofuran (5 ml). To the solution, acetic anhydride (0.07 g) was added and the mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with water and extracted twice with ethyl acetate. The organic phases were combined, washed with 2N hydrochloric acid and dried over magnesium sulfate. After filtering off the drying agent, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography to obtain 4-(acetamidomethyl)-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methyl-phenyl]benzamide (0.27 g, yield 77%).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washwashed with 2N hydrochloric acid
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtering off the drying agent
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was separated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-f88f90af22c0477ba814e9460eecd78e
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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