Water → (NE,R)-2-methyl-N-[(1-methylpyrazol-4-yl)methylidene]propane-2-sulfinamide

HRID 1051351Notes

Reaction equation

HRID 1051351 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 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 89998978(NE,R)-2-methyl-N-[(1-methylpyrazol-4-yl)methylidene]propane-2-sulfinamideYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-methyl-1H-pyrazole-4-carbaldehyde (2.2 g, 20 mmol) in THF (50 mL) was added (R)-2-methylpropane-2-sulfinamide (4.8 g, 40 mmol) and Ti(OEt)4 (9.2 g, 40 mmol). The reaction mixture was heated at 65° C. for 14 h. After cooling, the mixture was poured into water. The solid was filtered off, and the filtrate was extracted with EtOAc. The organic layer was concentrated and purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1) to afford 4.0 g (83%) of (R,E)-2-methyl-N-((1-methyl-1H-pyrazol-4-yl)methylene)propane-2-sulfinamide (46). LCMS (ESI) m/z: 214.1 [M+11]+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe solid was filtered off
  3. extractionthe filtrate was extracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified by SiO2 chromatography
  6. washeluting with petroleum ether/EtOAc (5:1)

Sources & evidence

ORD record
ord-4b4aff859e2846c583a7af96dd36abf9
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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