Toluene → HCID 12151385, compound

HRID 1392213Notes

Reaction equation

HRID 1392213 reaction equation
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:8].ClC1C=CC(C[NH:15][C:16](=[NH:18])[SH:17])=CC=1.[Cl:21][C:22]([SH:25])(Cl)Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OC)(C)(C)C.O>[Cl:8][C:4]1[CH:5]=[CH:6][C:1]([CH2:7][S:17][C:16]2[N:18]=[C:22]([Cl:21])[S:25][N:15]=2)=[CH:2][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 178479566HCID 178479566, compound

Product 1

HCID 12151385HCID 12151385, compound

Reagents, catalysts & solvents 3

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

Procedure

To the mixture of 80 ml of toluene and 40 ml of water, 10.0 g of 4-chlorobenzylisothiourea hydrochloride, 7.85 g of perchloromethylmercaptan and 192 mg of benzyltriethylammonium chloride were added, followed the solution of 6.75 g of sodium hydroxide dissolved to 40 ml of water was added dropwise over a period for 3 hours at about 0° C. 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 to obtain 5.38 g of 3-(4-chlorobenzyl)thio-5-chloro-1,2,4-thiadiazole.

Workup

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

Sources & evidence

ORD record
ord-61da534e491c42d5acc593b3d7d37a5f
Source dataset
uspto-grants-2008_03
Patent number
US07342031B2

Reaction notes

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