Triethylamine → HCID 44236572, compound

HRID 1617119Notes

Reaction equation

HRID 1617119 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[S-:11][C:12]#[N:13].[K+].[N:15]1([C:23]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][C:24]=2[NH2:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C>O.C(#N)C>[C:2]([NH:13][C:12]([NH:25][C:24]1[CH:26]=[C:27]([C:30]([F:31])([F:32])[F:33])[CH:28]=[CH:29][C:23]=1[N:15]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[S:11])(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516872Potassium thiocyanateHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 28514521HCID 28514521, compound

Product 1

HCID 44236572HCID 44236572, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
70 °C

Procedure

Isonicotinoyl chloride hydrochloride (261 mg, 1.47 mmol) was added to an acetonitrile solution (15 mL) of potassium thiocyanate (70.9 mg, 0.730 mmol) and then the mixture was stirred at 70° C. for 40 minutes. The organic mixture was left to room temperature. An acetonitrile solution (5 mL) of 2-(azacyclooctan-1-yl)-5-(trifluoromethyl)aniline (200 mg, 0.730 mmol) and triethylamine (205 μL, 1.47 mmol) were added sequentially. The reaction solution was heated to 50° C. and then stirred for 1 hour. The organic mixture was left to room temperature and then water was added to the solution. The mixture was subjected to extraction three times with ethyl acetate, washed with saturated sodium chloride solution, dried on anhydrous sodium sulfate, subjected to suction filtration, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1), so that (N-isonicotinoyl-N′-[2-(azacyclooctan-1-yl)-5-(trifluoromethyl)phenyl]thiourea (Compound 7) (149 mg, 46.8%) was obtained as yellow solid.

Workup

  1. waitThe organic mixture was left to room temperature
  2. temperatureThe reaction solution was heated to 50° C.
  3. stirringstirred for 1 hour
  4. waitThe organic mixture was left to room temperature
  5. extractionThe mixture was subjected to extraction three times with ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried on anhydrous sodium sulfate
  8. filtrationsubjected to suction filtration
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-076c3bbcd8e54f69adf36724c9c42a00
Source dataset
uspto-grants-2014_07
Patent number
US08765941B2

Reaction notes

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