Acetyl chloride → HCID 90410068, compound

HRID 516574Notes

Reaction equation

HRID 516574 reaction equation
C(Cl)(=O)C.C([NH:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[C:17]([F:22])[C:16]=2[F:23])[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28])(=O)C>CO>[NH2:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([I:21])=[C:17]([F:22])[C:16]=2[F:23])[N:12]=[C:11]([C:24]([O:26][CH3:27])=[O:25])[C:10]=1[Cl:28]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 90409635HCID 90409635, compound

Product 1

HCID 90410068HCID 90410068, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

Acetyl chloride (1.3 mL, 18 mmol, 10 equiv) was slowly added to methanol (12 mL) and stirred at 23° C. for 30 m. Methyl 4-acetamido-3-chloro-6-(2,3-difluoro-4-iodophenyl)picolinate (830 mg, 1.8 mmol, 1.0 equiv) was added and the heterogeneous white mixture was stirred at 23° C. for 18 h. The reaction mixture was concentrated by rotary evaporation. The residue was diluted with saturated sodium bicarbonate (200 mL) and extracted with dichloromethane (3×75 mL). The organic layer was dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation to afford the title compound as a white powder (720 mg, 95%).

Workup

  1. stirringthe heterogeneous white mixture was stirred at 23° C. for 18 h
  2. concentrationThe reaction mixture was concentrated by rotary evaporation
  3. additionThe residue was diluted with saturated sodium bicarbonate (200 mL)
  4. extractionextracted with dichloromethane (3×75 mL)
  5. dry with materialThe organic layer was dried (magnesium sulfate), gravity
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-02efa88139984275b228c451ffeb8e5d
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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