Dimethylformamide → N-t-butyl-4-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonamide

HRID 1516464Notes

Reaction equation

HRID 1516464 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:17]([C:21]1[NH:25][C:24]([CH:26]=[O:27])=[C:23]([Cl:28])[N:22]=1)[CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>CCOC(C)=O>[C:13]([NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:25]2[C:24]([CH:26]=[O:27])=[C:23]([Cl:28])[N:22]=[C:21]2[CH2:17][CH2:18][CH2:19][CH3:20])=[CH:4][CH:5]=1)(=[O:11])=[O:10])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 110012584-Bromomethyl-N-t-butyl-benzenesulfonamideHCID 178418251HCID 178418251, compound

Product 1

HCID 57931396N-t-butyl-4-(2-butyl-4-chloro-5-formylimidazol-1-ylmethyl)benzenesulfonamideYield 70.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Intermediate (2a) (13.6 g, 45 mmol, 1.0 eq), 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (8.4 g, 45 mmol, 1.0 eq) and potassium carbonate (12.4 g, 90 mmol, 2.0 eq) were added to 90 mL of DMF. The mixture was stirred at room temperature for 16 hours. The mixture was then diluted with 300 mL EtOAc and extracted with 100 mL 10% aq. LiCl, 2×200 mL water, 100 mL saturated aqueous NaCl, dried over MgSO4, and filtered. The filtrate was evaporated and purified by flash chromatography (40% EtOAc:hexanes) to yield intermediate (2b) (13.0 g). MS m/z: [M+H+] calcd for C19H26ClN3O3S, 412.1; found 412.4.

Workup

  1. extractionextracted with 100 mL 10% aq. LiCl, 2×200 mL water, 100 mL saturated aqueous NaCl
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. custompurified by flash chromatography (40% EtOAc:hexanes)

Sources & evidence

ORD record
ord-944a5e17a4bf46729d5df8946ba697b4
Source dataset
uspto-grants-2012_07
Patent number
US08227497B2

Reaction notes

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