Triethylamine → HCID 58792132, compound

HRID 2222136Notes

Reaction equation

HRID 2222136 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH3:8])[N:3]=1.[F:9][C:10]([F:18])([F:17])[CH:11]1[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]1.C(N(CC)CC)C>O1CCCC1>[CH3:8][S:7][C:4]1[N:3]=[C:2]([N:13]2[CH2:14][CH2:15][CH2:16][CH:11]([C:10]([F:18])([F:17])[F:9])[CH2:12]2)[S:6][N:5]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 27607763-(Trifluoromethyl)piperidine

Product 1

HCID 58792132HCID 58792132, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 3 ml of tetrahydrofuran were added 376 mg of 5-chloro-3-methylthio-1,2,4-thiadiazole, 230 mg of 3-trifluoromethylpiperidine and 1.52 g of triethylamine at room temperature. The mixture was stirred for 1.5 hour under reflux condition, and left as it for 14 hours at room temperature. The reaction mixture was extracted with ethyl acetate after the addition of water. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 398 mg of 3-methylthio-5-(3-trifluoromethylpiperidino)-1,2,4-thiadiazole.

Workup

  1. temperatureunder reflux condition
  2. waitleft as it for 14 hours at room temperature
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. additionafter the addition of water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b32e89be1874b23b327db592210491b
Source dataset
uspto-grants-2008_05
Patent number
US07371746B2

Reaction notes

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