Acryloyl chloride → HCID 22485556, compound

HRID 2181341Notes

Reaction equation

HRID 2181341 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[C:10]([O:22][CH3:23])[CH:9]=2)=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35].C(=O)([O-])O.[Na+]>C(Cl)Cl>[C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([O:22][CH3:23])[C:11]([O:16][CH2:17][C:18]([F:19])([F:20])[F:21])=[C:12]([O:14][CH3:15])[CH:13]=2)=[N:6][CH:7]=1)(=[O:36])[CH:34]=[CH2:35]

Participants

6

Reactant 4

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 22485528HCID 22485528, compound

Product 1

HCID 22485556HCID 22485556, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]pyridine (melting point: 176.0-177.5° C.)(28.2 g, 85.4 mmol) synthesized by a similar procedure to that described in Reference Example 11 in methylene chloride (550 mL) was added N,N-diisopropylethylamine (18.0 mL, 103 mmol). To the ice-cold stirred solution was added acryloyl chloride (7.00 mL, 86.0 mmol) dropwise over about 10 minutes. A saturated aqueous sodium hydrogencarbonate was added, and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Chloroform-hexane (1:2, 300 mL) was added to the residue and the resulting precipitate was collected by filtration to yield crude 5-acryloylamino-2-[3,5-dimethoxy-4-(2,2,2-trifluoroethoxy)phenyl]pyridine was obtained as colorless needles (melting point: 207.0-209.0° C.)(38.2 g).

Workup

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. additionChloroform-hexane (1:2, 300 mL) was added to the residue
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-409c89a6ba8149cc8cf90a2e24cd12af
Source dataset
uspto-grants-2005_05
Patent number
US06890940B2

Reaction notes

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