Toluene → 3-(Benzylsulfanyl)-5-chloro-1,2,4-thiadiazole

HRID 1392212Notes

Reaction equation

HRID 1392212 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C([NH:16][C:17](=[NH:19])[SH:18])C1C=CC=CC=1.[Cl:20][C:21]([SH:24])(Cl)Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OC)(C)(C)C.O>[CH2:7]([S:18][C:17]1[N:19]=[C:21]([Cl:20])[S:24][N:16]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 178479563Benzylthiourea hydrochloride

Product 1

HCID 121513833-(Benzylsulfanyl)-5-chloro-1,2,4-thiadiazole

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To the mixture of 20 ml of toluene and 10 ml of water, 2.02 g of benzylisothiourea hydrochloride, 1.86 g of perchloromethylmercaptan and 46 mg of benzyltriethylammonium chloride were added, followed the solution of 1.6 g of sodium hydroxide dissolved to 10 ml of water was added dropwise at about 0° C., and then stirred for 2 hours. Then, t-butylmethylether was added to the reaction mixture, and extracted. The organic layer was dried by anhydrous sodium salfate, and concentrated The residue obtaind was subjected to silica gel column chromatography (hexane:ethylacetate=20:1) to obtain 900 mg of 3-benzylthio-5-chloro-1,2,4-thiadiazole.

Workup

  1. additionwere added
  2. additionwas added dropwise at about 0° C.
  3. extractionextracted
  4. dry with materialThe organic layer was dried by anhydrous sodium salfate
  5. concentrationconcentrated The residue obtaind

Sources & evidence

ORD record
ord-4a19a770f18b4d79a1fd8b6e475e3f64
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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