Acetic Anhydride → HCID 54085736, compound

HRID 1378555Notes

Reaction equation

HRID 1378555 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:20]=[C:21]([CH2:25][C:26]([OH:28])=[O:27])[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>O>[F:18][C:19]1[CH:20]=[C:21]([C:25](=[CH:14][C:13]2[CH:16]=[CH:17][C:10]([S:9][CH3:8])=[CH:11][CH:12]=2)[C:26]([OH:28])=[O:27])[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 676173-Fluorophenylacetic acidHCID 769854-(Methylthio)benzaldehyde

Product 1

HCID 54085736HCID 54085736, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of acetic anhydride (60 mL), 4-(methylthio)benzaldehyde (4.99 g, 33 mmol), 3-fluorophenylacetic acid (5.08 g, 33 mmol), and triethylamine (3.98 g, 39 mmol) was heated to reflux for 4 hours. The reaction was cooled to 120° C., and water (120 mL) was added through an addition funnel. A yellow precipitate formed and, after further cooling to room temperature, was collected by filtration, washed with water, and recrystallized from toluene to give the desired intermediate as a yellow solid (3.72 g, 39%): mp 184°-187° C. 1H NMR (CDCl3) 300 MHz 7.92 (s,1H), 7.35 (m, 1H), 7.26 (d, J=6.3 Hz, 1H), 7.19 (d, J=7.7 Hz, 1H) 7.00 (m, 5H), 2.44 and 2.36 (s, 3H); 19F NMR (CDCl3) -112.61 (m). Mass spectrum M+H=289.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. customA yellow precipitate formed
  4. temperatureafter further cooling to room temperature
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-b40263ed78554334bc6a6cbd33692909
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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