Toluene → 2-Chloro-4-methyl-6-(methylthio)-1,3,5-triazine

HRID 1621361Notes

Reaction equation

HRID 1621361 reaction equation
[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[N:10]=[C:9](Cl)[N:8]=[C:7]([CH3:12])[N:6]=1.C1(C)C=CC=CC=1>O>[Cl:4][C:5]1[N:6]=[C:7]([CH3:12])[N:8]=[C:9]([S:2][CH3:1])[N:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 160832,4-Dichloro-6-methyl-1,3,5-triazineHCID 4378561Sodium methanethiolate

Product 1

HCID 127064372-Chloro-4-methyl-6-(methylthio)-1,3,5-triazineYield 78.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methanethiolate (0.49 g, 7.0 mmol) was added portionwise at 0° C. to a stirred cloudy solution of 2,4-dichloro-6-methyl-1,3,5-triazine (7) (1.04 g, 6.3 mmol) in toluene (10 mL, 94 mmol) over 15 min. After addition, the pale yellow mixture was stirred at the same temperature for another 1 h, and water (10 mL) was added. The separated aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give the crude residue which was purified with flash column chromatography (hexanes to 70% DCM in hexanes) to give 2-chloro-4-methyl-6-(methylthio)-1,3,5-triazine (0.87 g, 78% yield) as a white solid. MS (API-ES) m/z 176 (M+H)+; 1H NMR (d6-DMSO, 400 MHz) δ 2.55 (s, 3H) 2.51 (br. s., 3H).

Workup

  1. additionAfter addition
  2. extractionThe separated aqueous layer was extracted with EtOAc (2×20 mL)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give the crude residue which
  7. customwas purified with flash column chromatography (hexanes to 70% DCM in hexanes)

Sources & evidence

ORD record
ord-113b8f3de7f7472eb87822e084db9a94
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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