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

HRID 1811773Notes

Reaction equation

HRID 1811773 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-be091fb7a81f467899bb5cbace826a8f
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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