Triethylamine → HCID 69138960, compound

HRID 1246244Notes

Reaction equation

HRID 1246244 reaction equation
[F:1][C:2]1[C:3](/[CH:8]=[N:9]/[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:25]([O:28][CH2:29][C:30](Cl)=[O:31])(=[O:27])[CH3:26]>ClCCl>[C:25]([O:28][C@H:29]1[C@@H:8]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:30]1=[O:31])(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 178492247HCID 178492247, compound

Product 1

HCID 69138960HCID 69138960, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (2.29 l) of N-[(E)-(3-fluoro-2-pyridyl)methylidene]-4-methoxyaniline (449 g) and triethylamine (204 g) in dichloromethane was cooled to −10° C. Then acetoxyacetyl chloride (250 g) was added dropwise thereinto and the resultant mixture was stirred at the same temperature for 30 minutes. Then it was heated to room temperature and stirred for 16 hours. The liquid reaction mixture was washed with water and the solvent was concentrated under reduced pressure to thereby give a crude product (723 g). This crude product was recrystallized from a solvent mixture of ethanol (6.9 l) and ethyl acetate (350 ml) to thereby give the title compound (486 g) as brown crystals.

Workup

  1. customThe liquid reaction mixture
  2. washwas washed with water
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customto thereby give a crude product (723 g)
  5. customThis crude product was recrystallized from a solvent mixture of ethanol (6.9 l) and ethyl acetate (350 ml)

Sources & evidence

ORD record
ord-4b62c541b8594a209f15c12f81e510f8
Source dataset
uspto-grants-2006_10
Patent number
US07126003B2

Reaction notes

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