Bromomethylcyclopropane → HCID 57959845, compound

HRID 1698518Notes

Reaction equation

HRID 1698518 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[SH:7].Br[CH2:9][CH:10]1[CH2:12][CH2:11]1>C(O)C>[CH:10]1([CH2:9][S:7][C:3]2[N:2]([CH3:1])[CH:6]=[N:5][N:4]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 81503BromomethylcyclopropaneHCID 178481306HCID 178481306, compound

Product 1

HCID 57959845HCID 57959845, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 4-methyl-4H-1,2,4-triazole-3-thiol (5.2 g, 45 mmol) in absolute ethanol (30 mL) under nitrogen was added (bromomethyl)cyclopropane (4.50 mL, 46 mmol). The reaction was stirred at room temperature for 24 h and then concentrated in vacuo. The residue was partitioned between ethyl acetate and sat aq. Na2CO3 solution. The layers were separated and the aqueous phase further extracted with ethyl acetate (×3). The combined organic extracts were dried (MgSO4) and concentrated to give the title compound as a colourless oil (4.795 g, 28 mmol). 1H NMR (500 MHz, CDCl3) δ (ppm) 8.14 (1H, s), 3.62 (3H, s), 3.17 (2H, d, J=7.3 Hz), 1.27-1.15 (1H, m), 0.63-0.59 (2H, m), 0.30-0.27 (2H, m); m/z (ES+) 170 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate
  3. customThe layers were separated
  4. extractionthe aqueous phase further extracted with ethyl acetate (×3)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d4cde706044a4b8dab87c45a39388acc
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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