Hydrogen Sulfide → 2-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbothioamide

HRID 561202Notes

Reaction equation

HRID 561202 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17]#[N:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1.CCN(CC)CC.[SH2:32].CC[O-].[Na+].C(O)C>O1CCOCC1>[F:24][C:2]([F:23])([F:1])[C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[S:13][C:14]([C:17](=[S:32])[NH2:18])=[CH:15][N:16]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 5

HCID 402Hydrogen SulfideHCID 702EthanolHCID 8471TriethylamineHCID 2723922Sodium ethoxideHCID 666968312-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbonitrile

Product 1

HCID 866204572-{4-[2-(Trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbothioamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-{4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl}-1,3-thiazole-5-carbonitrile (354 mg, 1.0 mmol) in dioxane was added Et3N (20 μL, 0.14 mmol) and H2S (gas) was bubbled through the solution for about 1 min. After stirring at room temperature for 3 h, ethanol was added, followed by 21 wt. % NaOEt in ethanol (238 μL, 0.6 mmol). More H2S (gas) was bubbled through the solution for another minute. The mixture was then stirred at room temperature for 3 days. Volatile materials were removed in vacuo. The residue was dissolved in EtOAc, washed twice with water, dried (Na2SO4) and concentrated. Trituration with Et2O gave the title compound as a pale yellow solid.

Workup

  1. customwas bubbled through the solution for about 1 min
  2. additionethanol was added
  3. customMore H2S (gas) was bubbled through the solution for another minute
  4. stirringThe mixture was then stirred at room temperature for 3 days
  5. customVolatile materials were removed in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed twice with water
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-8dc18a5e28a3403c8b08b75f911fa23a
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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