Acetic Anhydride → HCID 67392294, compound

HRID 907386Notes

Reaction equation

HRID 907386 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=1.C(OC(=O)C)(=O)C.[OH-].[Na+]>[Cl-].[Zn+2].[Cl-].ClCCl>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 769854-(Methylthio)benzaldehydeHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 67392294HCID 67392294, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(methylsulfanyl)benzaldehyde (250 mg, 1.52 mmol), methyl 6-methylnicotinate (230 mg, 1.52 mmol), acetic anhydride (310 mg, 3.04 mmol) and a catalytic amount of zinc chloride was heated under reflux for 12 h. The reaction mixture was allowed to cool to room temperature before crushed ice was added followed by sodium hydroxide solution 10% (dropwise with stirring) until the mixture was basic (pH 8). Dichloromethane was added and the layers separated. The combined organic layers were collected, dried (MgSO4) and concentrated under reduced pressure to give the crude product as brown solid. The crude mixture was purified by column chromatography (ethyl acetate/n-hexane, 1:1, RF=0.80), followed by recrystallization from methanol to give the sub-title compound as pale yellow crystals (251 mg, 58%).

Workup

  1. temperatureunder reflux for 12 h
  2. custombefore crushed ice
  3. additionwas added
  4. customthe layers separated
  5. customThe combined organic layers were collected
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product as brown solid
  9. customThe crude mixture was purified by column chromatography (ethyl acetate/n-hexane, 1:1, RF=0.80)
  10. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-f065409ff4114f4998a119c1f0672882
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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