Methyl iodide → HCID 178503580, compound

HRID 477745Notes

Reaction equation

HRID 477745 reaction equation
[OH-].[Na+].[CH2:3]([S:10][C:11]1[N:15]=[C:14]([SH:16])[NH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:17]I>O.ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:3]([S:10][C:11]1[N:15]=[C:14]([S:16][CH3:17])[NH:13][N:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178527897HCID 178527897, compound

Product 1

HCID 178503580HCID 178503580, compoundYield 85.1%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of sodium hydroxide (16 g) in water (60 ml) was added to a suspension of 3-benzylthio-5-mercapto-1,2,4-triazole (89.2 g) in dichloromethane (400 ml) containing benzyltriethylammonium chloride (1 g) with stirring and cooling to 15°-20° C. To this mixture methyl iodide (56.8 g) was added, and stirring was continued at room temperature for 24 hours. The dichloromethane phase was separated, washed with water twice, dried over magnesium sulphate and run down to give 94 g of crude product, which was recrystallised from toluene to give 80.7 g of desired product, mp 80°-82° C.

Workup

  1. temperaturecooling to 15°-20° C
  2. stirringstirring
  3. customThe dichloromethane phase was separated
  4. washwashed with water twice
  5. dry with materialdried over magnesium sulphate
  6. customto give 94 g of crude product, which
  7. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-98b0ffbf77e04d01b7e7b8e3b4d6a01f
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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