Sodium Carbonate → HCID 67260636, compound

HRID 2359090Notes

Reaction equation

HRID 2359090 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:11]=[C:10]([CH3:12])[NH:9][N:8]=2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>>[Br:13][C:11]1[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:8][NH:9][C:10]=1[CH3:12]

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 5260620HCID 5260620, compound

Product 1

HCID 67260636HCID 67260636, compoundYield 64%

Conditions

Temperature
0 °C

Procedure

3-(5-chloro-2-thienyl)-5-methyl-1H-pyrazole (111 mmol) was dissolved in 200 mL dry 1V, N-dim ethyl formamide and cooled to 0° C. under nitrogen atmosphere. N-Bromosuccinimide (118 mmol) was added in small portions at 0° C. The reaction mixture was allowed to warm to room temperature and was stirred overnight. The solution was poured into a mixture of saturated aqueous sodium thiosulfate solution and saturated aqueous sodium carbonate solution (1:1) at room temperature. The precipitate was filtered, washed thoroughly with water, dissolved in ethyl acetate, dried over MgSO4, filtered and evaporated to afford 19.5 g of 4-bromo-3-(5-chloro-2-thienyl)-5-methyl-1H-pyrazole (64% yield) that was used without further purification.

Workup

  1. dry with materialdry 1V, N-dim ethyl formamide
  2. temperatureto warm to room temperature
  3. filtrationThe precipitate was filtered
  4. washwashed thoroughly with water
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-67db3595fcbf47efa54ca45bfcae3530
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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