tert-Butylsulfinamide, (S)-(-)- → HCID 87300988, compound

HRID 2425553Notes

Reaction equation

HRID 2425553 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[CH:8]=O.[CH3:10][C:11]([S@@:14]([NH2:16])=[O:15])([CH3:13])[CH3:12]>C1COCC1>[Cl:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1/[CH:8]=[N:16]/[S@:14]([C:11]([CH3:13])([CH3:12])[CH3:10])=[O:15]

Participants

4

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 151450195-Chloro-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 87300988HCID 87300988, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde (500 mg, 3.46 mmol) was suspended in THF (20 ml), Ti(OEt)4 (1.51 ml, 7.26 mmol) was added followed by (S)-(+)-2-methyl-2-propanesulfinamide (440 mg, 3.63 mmol) and the reaction heated to reflux for 6 hours. The reaction was then cooled to room temperature, poured onto EtOAc:Brine (20 ml: 20 ml) filtered through celite and washed through with EtOAc (2×20 ml). The organic layer was then separated, washed with brine (20 ml), dried over Na2SO4, filtered and concentrated to give the title compound as a brown viscous oil (760 mg, 88.7% yield). 1H NMR (400 MHz, CDCl3) 1.22-1.23 (9H s) 3.88 (3H s) 7.92 (1H s) 8.43 (1H br. s) MS (ESI/APCI) m/z 248 (M+H)+

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 6 hours
  3. additionpoured onto EtOAc
  4. filtrationBrine (20 ml: 20 ml) filtered through celite
  5. washwashed through with EtOAc (2×20 ml)
  6. customThe organic layer was then separated
  7. washwashed with brine (20 ml)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5b83f83663f841dcacaad74957a52e9d
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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