tert-Butylsulfinamide, (R)-(+)- → (R)-N-((1-(4-methoxyphenyl)-1H-imidazol-2-yl)methylene)-2-methylpropane-2-sulfinamide

HRID 1506623Notes

Reaction equation

HRID 1506623 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=O)=[CH:5][CH:4]=1.[CH3:16][C:17]([S@:20]([NH2:22])=[O:21])([CH3:19])[CH3:18]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[CH:14]=[N:22][S@@:20]([C:17]([CH3:19])([CH3:18])[CH3:16])=[O:21])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 280632501-(4-Methoxyphenyl)-1h-imidazole-2-carbaldehyde

Product 1

HCID 90281518(R)-N-((1-(4-methoxyphenyl)-1H-imidazol-2-yl)methylene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(4-methoxyphenyl)-1H-imidazole-2-carbaldehyde (200 mg, 1 mmol), (R)-2-methylpropane-2-sulfinamide (145 mg, 1.2 mmol), and CuSO4 (160 mg, 1 mmol) were combined in DCM (5 mL). The reaction was stirred at ambient temperature for 15 hr. The reaction was filtered, solvents removed in vacuo, and the residue purified by column chromatography on silica to provide the desired product: MS (m/z) 305.9 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. customsolvents removed in vacuo
  3. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-34a04c77e2c64f79913bf5ed95ca1db1
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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