Thiomorpholine → HCID 69217583, compound

HRID 2222137Notes

Reaction equation

HRID 2222137 reaction equation
ClC1SN=C(SC)N=1.ClC1C=CC=C(C(OO)=O)C=1.Cl[C:21]1[S:25][N:24]=[C:23]([S:26]([CH3:29])(=[O:28])=[O:27])[N:22]=1.Cl[C:31]1[S:35][N:34]=[C:33]([S:36]([CH3:38])=[O:37])[N:32]=1.[NH:39]1[CH2:44][CH2:43][S:42][CH2:41][CH2:40]1>O.C(Cl)(Cl)Cl>[CH3:29][S:26]([C:23]1[N:22]=[C:21]([N:39]2[CH2:44][CH2:43][S:42][CH2:41][CH2:40]2)[S:25][N:24]=1)(=[O:28])=[O:27].[CH3:38][S:36]([C:33]1[N:32]=[C:31]([N:39]2[CH2:44][CH2:43][S:42][CH2:41][CH2:40]2)[S:35][N:34]=1)=[O:37]

Participants

9

Reactant 5

HCID 67164ThiomorpholineHCID 70297m-Chloroperbenzoic acidHCID 5709535-Chloro-3-(methylsulfanyl)-1,2,4-thiadiazoleHCID 27612875-chloro-3-methylsulfonyl-1,2,4-thiadiazole2×HCID 15240612HCID 15240612, compound2×

Product 2

HCID 69217583HCID 69217583, compoundHCID 69219894HCID 69219894, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

With 12 ml of chloroform was mixed 1.0 g of 5-chloro-3-methylthio-1,2,4-thiadiazole, and 2.59 g of 3-chloroperbenzoic acid (content: 70-75 weight %) was added under ice-cooling. The mixture was stirred at room temperature for 2.25 hours and left as it was for 15 hours to obtain a crude mixture of 5-chloro-3-methylsulfonyl-1,2,4-thiadiazole and 5-chloro-3-methylsulfinyl-1,2,4-thiadiazole. Into the crude mixture of 5-chloro-3-methylsulfonyl-1,2,4-thiadiazole and 5-chloro-3-methylsulfinyl-1,2,4-thiadiazole was added 2.46 g of thiomorpholine dropwise under water-cooling. The mixture was stirred for 1 hour at room temperature. The reaction mixture was extracted with chloroform after the addition of saturated sodium bicarbonate aqueous solution. 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 1.08 g of 3-methylsulfonyl-5-thiomorpholino-1,2,4-thiadiazole and 6 mg of 3-methylsulfinyl-5-thiomorpholino-1,2,4-thiadiazole.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. waitleft as it
  4. waitwas for 15 hours
  5. customto obtain a crude
  6. temperaturecooling
  7. stirringThe mixture was stirred for 1 hour at room temperature
  8. extractionThe reaction mixture was extracted with chloroform
  9. additionafter the addition of saturated sodium bicarbonate aqueous solution
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f7eb7b7d3444a7dbae429f8e2fb0981
Source dataset
uspto-grants-2008_05
Patent number
US07371746B2

Reaction notes

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