Bromine → HCID 11254215, compound

HRID 1951173Notes

Reaction equation

HRID 1951173 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8](=O)[CH3:9])=[CH:3][CH:2]=1.BrBr.[N:13]1[CH:18]=[CH:17][N:16]=[CH:15][C:14]=1[NH:19][C:20]([NH2:22])=[S:21]>O1CCOCC1>[CH3:9][C:8]1[N:22]=[C:20]([NH:19][C:14]2[CH:15]=[N:16][CH:17]=[CH:18][N:13]=2)[S:21][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 805524-PyridinylacetoneHCID 2771013N-Pyrazinylthiourea

Product 1

HCID 11254215HCID 11254215, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-pyridin-4-yl-propan-2-one (0.1 g, 0.812 mmol) in dioxane (7 ml) is added bromine (0.029 ml, 0.569 mmol) dropwise. After 45 minutes, the solvent is removed in vacuo and the crude product is dissolved in ethanol (15 ml). The solution is treated with pyrazin-2-yl-thiourea (0.125 g, 0.812 mmol) and the reaction mixture is heated at 60° C. for 3 hours. The solvent is removed in vacuo and purification by chromatography on silica, eluting with ethyl acetate-methanol affords the titled compound.

Workup

  1. customthe solvent is removed in vacuo
  2. dissolutionthe crude product is dissolved in ethanol (15 ml)
  3. customThe solvent is removed in vacuo and purification by chromatography on silica
  4. washeluting with ethyl acetate-methanol

Sources & evidence

ORD record
ord-b38a63c4e8674504a5ed42f9adfb254d
Source dataset
uspto-grants-2013_03
Patent number
US08404684B2

Reaction notes

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