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

HRID 623295Notes

Reaction equation

HRID 623295 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[NH:16])=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:24][C:25]([Cl:30])([Cl:29])[C:26](Cl)=[O:27].O>ClCCl>[Cl:24][C:25]([Cl:30])([Cl:29])[C:26]([N:16]=[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]1[CH2:9][C:6]1[CH:7]=[N:8][C:3]([Cl:2])=[CH:4][CH:5]=1)=[O:27]

Participants

6

Reactant 4

HCID 962Water2×HCID 6420Trichloroacetyl chlorideHCID 8471TriethylamineHCID 866869301-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride

Product 1

HCID 896130972,2,2-trichloro-N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-acetamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

70 mg (0.27 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1 was dissolved in 4 ml of anhydrous dichloromethane, 94 μl (0.68 mmol, 68 mg) of triethylamine and 33 g (0.27 mmol, 49 mg) of trichloroacetyl chloride were added thereto in sequence, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, water was added thereto to stop the reaction and liquid separation was performed with dichloromethane and water. The organic layer was washed once with water and twice with 1% hydrochloric acid, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Diethyl ether was added thereto to precipitate a solid, and thus the solid was collected and dried to obtain the subject material. Amount obtained 61 mg (yield 62%).

Workup

  1. customthe reaction and liquid separation
  2. washThe organic layer was washed once with water and twice with 1% hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionDiethyl ether was added
  6. customto precipitate a solid
  7. customthus the solid was collected
  8. customdried
  9. customto obtain the subject material
  10. customAmount obtained 61 mg (yield 62%)

Sources & evidence

ORD record
ord-e0110b7b7b7a4c6ba457b86c8afcb6fd
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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