Methanol → 5-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazole

HRID 1661064Notes

Reaction equation

HRID 1661064 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8]2[N:9]([CH3:14])[C:10]([SH:13])=[N:11][N:12]=2)=[C:5]([CH3:7])[N:6]=1.CO.C([O-])([O-])=O.[K+].[K+].Br[CH2:24][CH2:25][CH2:26][Cl:27]>C(OCC)(=O)C.CC(C)=O>[Cl:27][CH2:26][CH2:25][CH2:24][S:13][C:10]1[N:9]([CH3:14])[C:8]([C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])=[N:12][N:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 178432727HCID 178432727, compound

Product 1

HCID 446278985-(5-(3-chloropropylthio)-4-methyl-4H-1,2,4-triazol-3-yl)-2,4-dimethylthiazoleYield 37.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

5-(2,4-dimethylthiazol-5-yl)-4-methyl-4H-1,2,4-triazole-3-thiol (Prep27, 5 g, 22 mmol) was added to a mixture of methanol (15 ml) and acetone (35 ml), followed by K2CO3 (5 g, 36 mmol) and 1-bromo-3-chloropropane (35 ml, 36 mmol). The suspension was stirred at 22° C. for 24 h. The volume of solvent was reduced, then ethyl acetate (63 ml) was added and the organic layer was washed with water, the EA was removed under vacuum and the crude purified by FC (EA/MeOH 15:1) to afford 2.5 g of pure product (y=37%).

Workup

  1. washthe organic layer was washed with water
  2. customthe EA was removed under vacuum
  3. customthe crude purified by FC (EA/MeOH 15:1)

Sources & evidence

ORD record
ord-10eff361006c4b3ea2b609b2d6ddd6a3
Source dataset
uspto-grants-2011_10
Patent number
US08030322B2

Reaction notes

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