tert-Butylsulfinamide, (R)-(+)- → HCID 87300875, compound

HRID 2425551Notes

Reaction equation

HRID 2425551 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 10964479tert-Butylsulfinamide, (R)-(+)-HCID 151450195-Chloro-1-methyl-1H-pyrazole-4-carbaldehyde

Product 1

HCID 87300875HCID 87300875, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-chloro-1-methyl-1H-pyrazole-4-carbaldehyde (1130 mg, 7.82 mmol) was suspended in THF (20 ml), Ti(OEt)4 (4.29 ml, 16.4 mmol) was added followed by (R)-(+)-2-methyl-2-propanesulfinamide and the reaction heated to reflux for 18 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 (1690 mg, 87.3% 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 18 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-c361a066ad984762a7e8d0689c8a539f
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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