Toluene → HCID 12151387, compound

HRID 917343Notes

Reaction equation

HRID 917343 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+].[CH3:29][O:30]C(C)(C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:22][C:23]1[S:26][N:19]=[C:17]([S:18][CH2:7][C:1]2[CH:6]=[CH:5][C:4]([O:30][CH3:29])=[CH:3][CH:2]=2)[N:16]=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

Into the mixture of 20 ml of toluene and 10 ml of water were added 2.53 g of 4-methoxybenzylisothiourea hydrogen chloride, 2.03 g of perchloromethyl mercaptan, and 50 mg of benzyltriethylammonium chloride, and a solution of 1.74 g of sodium hydroxide in 10 ml of water was added dropwise to the mixture at about 0° C. over 4 hours. After the addition, the mixture was stirred for 1 hour at room temperature. Into the reaction mixture was added t-butyl methyl ether, and extracted. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the residue obtained was subjected to silica gel column chromatography to give 5.38 g of 5-chloro-3-(4-methoxybenzyl)thio-1,2,4-thiadiazole.

Workup

  1. additionAfter the addition
  2. extractionextracted
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customthe residue obtained

Sources & evidence

ORD record
ord-e6a2980e50c74c5390dc54b7f5f83ae0
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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