Acetic Anhydride → HCID 53682281, compound

HRID 1378557Notes

Reaction equation

HRID 1378557 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][S:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[CH2:26][C:27]([OH:29])=[O:28].C(N(CC)CC)C>O>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26](=[CH:14][C:13]1[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=1)[C:27]([OH:29])=[O:28]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 769854-(Methylthio)benzaldehydeHCID 1235812,4-Difluorophenylacetic acid

Product 1

HCID 53682281HCID 53682281, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of acetic anhydride (50 mL), 4-(methylthio)benzaldehyde (3.75 g, 24.6 mmol), 2,4-difluorophenylacetic acid (4.41 g, 24.6 mmol), and triethylamine (2.80 g, 27.7 mmol) was heated to reflux for 3.5 hours. The reaction was cooled to 90° C., and water (100 mL) was added through an addition funnel. A yellow oil formed that solidified upon stirring. The solid was collected by filtration, and dissolved in ethyl acetate, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The solid thus obtained was recrystallized from toluene to give the desired acid (3.18 g, 42%): mp 165°-171° C. 1H NMR (acetone-d6) 300 MHz 7.95 (s,1H), 7.08-7.18 (m, 7H), 2.47 and 2.31 (s, 3H); 19F NMR (acetone-d6) -110.81 (m) -111.75 (m). Mass spectrum: M+H=306.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hours
  3. customA yellow oil formed
  4. filtrationThe solid was collected by filtration
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe solid thus obtained
  10. customwas recrystallized from toluene

Sources & evidence

ORD record
ord-7673999b888c4d40ab9323bc378fbad2
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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