Water → HCID 89989328, compound

HRID 1051350Notes

Reaction equation

HRID 1051350 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=O)[CH:4]=[N:3]1.[CH3:9][C:10]([S@@:13]([NH2:15])=[O:14])([CH3:12])[CH3:11].O>C1COCC1>[CH3:9][C:10]([S@@:13](/[N:15]=[CH:7]/[C:5]1[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=1)=[O:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 5731171-Methyl-1H-pyrazole-4-carbaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 89989328HCID 89989328, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (3.0 g, 27 mmol) in THF (100 mL) was added (S)-2-methylpropane-2-sulfinamide (6.6 g, 54 mmol) and Ti(OEt)4 (22.3 g, 98.0 mmol). The reaction mixture was heated at 65° C. for 12 h. After cooling, the mixture was poured into water. The solid was filtered, and the filtrate was extracted with EtOAc (3×100 mL). The organic layer was washed with water (3×50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (4:1) to afford 5.6 g (98%) of (S,E)-2-methyl-N-((1-methyl-1H-pyrazol-4-yl)methylene)propane-2-sulfinamide 40 as colorless oil. LCMS (ESI) m/z: 214.1 [M+H]+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was filtered
  3. extractionthe filtrate was extracted with EtOAc (3×100 mL)
  4. washThe organic layer was washed with water (3×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with petroleum ether/EtOAc (4:1)

Sources & evidence

ORD record
ord-cb01351970214bea9def631c64357274
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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