1-methyl-1H-imidazole-5-carbaldehyde → (NE,R)-2-methyl-N-[(3-methylimidazol-4-yl)methylidene]propane-2-sulfinamide

HRID 1051386Notes

Reaction equation

HRID 1051386 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]=O)=[CH:5][N:4]=[CH:3]1.[CH3:9][C:10]([S@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH3:9][C:10]([S@:13](/[N:15]=[CH:7]/[C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)=[O:14])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 5735921-methyl-1H-imidazole-5-carbaldehydeHCID 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89999199(NE,R)-2-methyl-N-[(3-methylimidazol-4-yl)methylidene]propane-2-sulfinamideYield 51.1%

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-methyl-1H-imidazole-5-carbaldehyde (1.46 g, 13.26 mmol), (R)-2-methylpropane-2-sulfinamide (2.893 g, 23.87 mmol), and tetraethoxytitanium (10.89 g, 47.73 mmol) in THF (100 mL) was heated to 65° C. for 12 h. The reaction was cooled and poured onto water. The solids were filtered off, and the filtrate was extracted with EtOAc. The layers were separated, and the organic layer was concentrated. The resulting residue was purified by SiO2 eluting with a DCM/MeOH gradient (1.5 to 2% MeOH) to afford 1.444 g (51.1%) of (R,E)-2-methyl-N-((1-methyl-1H-imidazol-5-yl)methylene)propane-2-sulfinamide (128).

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured onto water
  3. filtrationThe solids were filtered off
  4. extractionthe filtrate was extracted with EtOAc
  5. customThe layers were separated
  6. concentrationthe organic layer was concentrated
  7. customThe resulting residue was purified by SiO2 eluting with a DCM/MeOH gradient (1.5 to 2% MeOH)

Sources & evidence

ORD record
ord-e5c6ac61843045c8b47b888d24f9252e
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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