Acetic Anhydride → HCID 58054293, compound

HRID 75113Notes

Reaction equation

HRID 75113 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=[O:9])=O.C(OC(=O)C)(=O)C>>[F:1][C:2]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:3]=1[C:4]1[O:9][C:8](=[O:10])[CH2:7][N:6]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 167701812-(2,5-Difluorobenzamido)acetic acid

Product 1

HCID 58054293HCID 58054293, compound

Conditions

Temperature
100 °C

Procedure

A 100 mL round-bottomed flask was charged with 2-(2,5-difluorobenzamido)acetic acid (1.7 g, 7.9 mmol) and acetic anhydride (7.46 mL, 79 mmol). The resulting suspension was heated to 100° C. for 20 minutes (during which time the solids had all dissolved) and cooled to room temperature. The mixture was concentrated in vacuo and azeotroped with toluene and dried under vacuum for a weekend. This yielded an orange-colored oil that was used without further purification. An analytical sample was obtained by trituration with tert-butyl methyl ether. 1H-NMR (CDCl3) δ 7.34 (m, 1H), 7.19-7.04 (m, 2H), 4.38 (d, 2H).

Workup

  1. dissolutionall dissolved) and
  2. temperaturecooled to room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. customazeotroped with toluene
  5. customdried under vacuum for a weekend
  6. customThis yielded an orange-colored oil that
  7. customwas used without further purification
  8. customAn analytical sample was obtained by trituration with tert-butyl methyl ether

Sources & evidence

ORD record
ord-d2ff67da00204487a14abec0952ceae9
Source dataset
uspto-grants-2014_09
Patent number
US08835422B2

Reaction notes

Loading…