Acetone → HCID 66743319, compound

HRID 2364061Notes

Reaction equation

HRID 2364061 reaction equation
[Br:1][C:2]1[S:6][C:5](C(N)=O)=[C:4]([NH:10][CH3:11])[C:3]=1[CH3:12].[CH3:13][C:14]([CH3:16])=O.[O-]S([O-])(=O)=O.[Mg+2].CC1C=CC(S(O)(=O)=O)=CC=1.[C:34]([O-:37])(O)=O.[Na+].C[N:40](C=O)C>>[Br:1][C:2]1[S:6][C:5]2[C:34](=[O:37])[NH:40][C:14]([CH3:16])([CH3:13])[N:10]([CH3:11])[C:4]=2[C:3]=1[CH3:12]

Participants

7

Reactant 6

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 66743876HCID 66743876, compound

Product 1

HCID 66743319HCID 66743319, compoundYield 43%

Conditions

Temperature
60 °C

Procedure

A mixture of 5-bromo-4-methyl-3-(methylamino)thiophene-2-carboxamide (2.34 g, 9.39 mmol), acetone (10 mL, 136 mmol), MgSO4 (1.13 g, 9.39 mmol), PTSA (0.089 g, 0.47 mmol) and DMF (10 mL) was stirred at 60° C. overnight. The mixture was poured into saturated aqueous NaHCO3 and extracted with EtOAc, and the extract was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, NH, 98:2 hexane/EtOAc to 50:50 hexane/EtOAc) to afford the title compound (1.17 g, 43%) as a pale orange solid:

Workup

  1. extractionextracted with EtOAc
  2. dry with materialthe extract was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (Purif, NH, 98:2 hexane/EtOAc to 50:50 hexane/EtOAc)

Sources & evidence

ORD record
ord-122df6168b5c4a5d81b883ac19a22c42
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

Loading…