Toluene → HCID 12151387, compound

HRID 1392214Notes

Reaction equation

HRID 1392214 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.COC1C=CC(C[NH:16][C:17](=[NH:19])[SH:18])=CC=1.[Cl:22][C:23]([SH:26])(Cl)Cl.[OH-].[Na+].[C:29]([O:33]C)(C)(C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[CH3:29][O:33][C:4]1[CH:5]=[CH:6][C:1]([CH2:7][S:18][C:17]2[N:19]=[C:23]([Cl:22])[S:26][N:16]=2)=[CH:2][CH:3]=1

Participants

8

Reactant 5

HCID 1140TolueneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 178491143HCID 178491143, compound

Product 1

HCID 12151387HCID 12151387, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

To the mixture of 20 ml of toluene and 10 ml of water, 2.53 g of 4-methoxybenzylisothiourea hydrochloride, 2.03 g of perchloromethylmercaptan and 50 mg of benzyltriethylammonium chloride were added, followed the solution of 1.74 g of sodium hydroxide dissolved to 10 ml of water was added dropwise over a period for 4 hours at about 0° C. After completion of addition, the mixture was stirred at room tempareture for 1 hour. Then, t-butylmethylether was added to the reaction mixture, and extracted. The organic layer was dried by anhydrous sodium salfate. The concentrated residue obtaind was subjected to silica gel column chromatography to obtain 5.38 g of 3-(4-methoxybenzyl)thio-5-chloro-1,2,4-thiadiazole.

Workup

  1. additionwere added
  2. additionwas added dropwise over a period for 4 hours at about 0° C
  3. additionAfter completion of addition
  4. extractionextracted
  5. dry with materialThe organic layer was dried by anhydrous sodium salfate

Sources & evidence

ORD record
ord-736b4b315c2a4a5aa050073e3638a42d
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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