Bromine → HCID 67170996, compound

HRID 872573Notes

Reaction equation

HRID 872573 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[NH:6][N:5]=1)(=O)[CH3:2].BrBr.BrC(Br)C(C1C=C(C(OC)=O)NN=1)=O.[C:29]([NH2:32])(=[S:31])[CH3:30]>C(Cl)(Cl)Cl.CO>[CH3:30][C:29]1[S:31][CH:2]=[C:1]([C:4]2[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[NH:6][N:5]=2)[N:32]=1

Participants

7

Reactant 4

HCID 24408BromineHCID 2723949ThioacetamideHCID 16767345Methyl 3-acetyl-1H-pyrazole-5-carboxylateHCID 87295224HCID 87295224, compound

Product 1

HCID 67170996HCID 67170996, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

Methyl 3-acetyl-1H-pyrazole-5-carboxylate (100 mg, 0.595 mmol) was refluxed with bromine (143 mg, 0.892 mmol) in chloroform. Solvent was evaporated and thus obtained methyl 3-(2,2-dibromoacetyl)-1H-pyrazole-5-carboxylate (191 mg, 0.586 mmol) was treated with thioacetamide (44 mg, 0.586 mmol) in refluxing methanol. Solvent was evaporated and the residue was dissolved in DCM and washed with water. Organic phase was dried over Na2SO4, filtered and evaporated to give 133 mg (102%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 2.71 (s, 3H), 3.83 (s, 3H), 7.10 (s, 1H), 7.90 (s, 1H) 14.0 (broad s, 1H).

Workup

  1. customSolvent was evaporated
  2. customSolvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. washwashed with water
  5. dry with materialOrganic phase was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-1243a407f88c4e649dd09de594805c30
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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