Dichloromethane → N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(2H)-ylidene]acetamide

HRID 1519019Notes

Reaction equation

HRID 1519019 reaction equation
ClCCl.Cl.[Cl:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=[NH:19])=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>O>[Cl:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]2=[N:19][C:27](=[O:29])[CH3:28])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866869301-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride

Product 1

HCID 86686933N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(2H)-ylidene]acetamideYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Anhydrous dichloromethane (20 mL) was added to 118 mg (0.46 mmol) of 1-[(6-chloropyridin-3-yl)methyl]pyridine-2(1H)-imine hydrochloride obtained by the alternative method described in Synthesis Example 14, following which 159 μL (1.16 mmol, 116 mg) of triethylamine and 33 μL of acetyl chloride were added and the mixture was stirred at room temperature for 15 minutes. The reaction was stopped by adding water to the reaction mixture, and liquid-liquid extraction was carried out with chloroform and water. The organic phase was washed with a saturated aqueous solution of ammonium chloride, then concentrated. With the addition of hexane thereto, a solid settled out. The solid was collected by filtration and washed, then thoroughly dried, giving 21 mg of the target compound (yield, 17%).

Workup

  1. customobtained by the alternative method
  2. customdescribed in Synthesis Example 14
  3. additionwere added
  4. extractionto the reaction mixture, and liquid-liquid extraction
  5. washThe organic phase was washed with a saturated aqueous solution of ammonium chloride
  6. concentrationconcentrated
  7. additionWith the addition of hexane
  8. filtrationThe solid was collected by filtration
  9. washwashed
  10. customthoroughly dried

Sources & evidence

ORD record
ord-798223cc0c194f80803c1d04d605d162
Source dataset
uspto-grants-2015_07
Patent number
US09073866B2

Reaction notes

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