Water → HCID 117830942, compound

HRID 515916Notes

Reaction equation

HRID 515916 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:14]=[CH:13][N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:11]=1[C:25]#[N:26].S(=O)(O)[O-].[Na+].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:14]1[C:10]([CH3:9])=[C:11]([C:25]#[N:26])[N:12]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 16093753HCID 16093753, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 117830942HCID 117830942, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Bromosuccinimide (12.0 g, 67.4 mmol) is added all at once to a suspension of 3-methyl-1-(4-methylbenzenesulphonyl)-1H-pyrrole-2-carbonitrile (14.45 g, 55.6 mmol) in N,N-dimethylformamide (60 mL) at ambient temperature. The mixture is stirred at ambient temperature for 29 hours and is then cooled in an ice bath. Saturated aqueous sodium bisulphite solution (90 mL), water (90 mL) and ethyl acetate (250 mL) are then added. The phases are separated, and then the aqueous phase is extracted with ethyl acetate (2×70 mL). The combined organic phases are washed with 5% aqueous potassium bicarbonate solution (90 mL), water (3×90 mL), and then brine (3×90 mL). The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. The crude product is purified by chromatography over silica gel using toluene and heptane as eluants to obtain the expected compound in the form of a solid.

Workup

  1. temperatureis then cooled in an ice bath
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl acetate (2×70 mL)
  4. washThe combined organic phases are washed with 5% aqueous potassium bicarbonate solution (90 mL), water (3×90 mL)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-0604fe7fbec6466485f7a91eb828ab30
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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