Dimethyl Sulfate → HCID 54170383, compound

HRID 978928Notes

Reaction equation

HRID 978928 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:16])[C:6]=1[NH:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]([SH:15])=[N:11][N:10]=1.[OH-].[Na+].[CH3:19]OS(OC)(=O)=O>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C1(C)C=CC=CC=1>[CH3:1][C:2]1[S:3][CH:4]=[C:5]([CH3:16])[C:6]=1[NH:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]([S:15][CH3:19])=[N:11][N:10]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 178431903HCID 178431903, compound

Product 1

HCID 54170383HCID 54170383, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 9.5 g (0.037 mol) N-(2,4-dimethyl-thien-3-yl)-N-(4-methyl-5-mercapto-1,2,4-triazol-3-yl-methyl)-amine, 1.1 g triethyl-benzyl ammonium chloride in 100 ml toluene and 30 ml aqueous 50% sodium hydroxide solution are added 4.7 g (0.037 mol) dimethylsulfate. The reaction mixture is stirred at room temperature for 5 hours, the organic layer is separated, washed with three 100 ml portions of water, dried over Na2SO4 and evaporated to dryness. The residue is recrystallized twice from ether giving the pure title compound, m.p. 92°-96° C.

Workup

  1. customthe organic layer is separated
  2. washwashed with three 100 ml portions of water
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue is recrystallized twice from ether giving the pure title compound, m.p. 92°-96° C.

Sources & evidence

ORD record
ord-3a6ae722cd334fdabafa3b85ebd9eabf
Source dataset
uspto-grants-1987_05
Patent number
US04666502

Reaction notes

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