Tert-Butanesulfinamide → HCID 88924920, compound

HRID 715057Notes

Reaction equation

HRID 715057 reaction equation
[O:1]1[C:5]([CH:6]=O)=[CH:4][N:3]=[CH:2]1.[CH3:8][C:9]([S:12]([NH2:14])=[O:13])([CH3:11])[CH3:10]>C1COCC1.C(O[Ti](OCC)(OCC)OCC)C>[CH3:8][C:9]([S:12](/[N:14]=[CH:6]/[C:5]1[O:1][CH:2]=[N:3][CH:4]=1)=[O:13])([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 118293725-OXAZOLECARBOXALDEHYDE

Product 1

HCID 88924920HCID 88924920, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 178477244HCID 178477244, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Oxazole-5-carbaldehyde (1.0 g, 10.30 mmol), 2-methylpropane-2-sulfinamide (2.247 g, 18.54 mmol; CASRN 146374-27-8), and tetraethoxytitanium (8.460 g, 37.09 mmol) were stirred in THF (15 mL) and heated to 65° C. for 12 h under nitrogen. 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 dried (MgSO4), filtered and concentrated. The resulting residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (20 to 25% EtOAc) to afford 1.211 g (58.7%) of (E)-2-methyl-N-(oxazol-5-ylmethylene)propane-2-sulfinamide (20).

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. dry with materialthe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (20 to 25% EtOAc)

Sources & evidence

ORD record
ord-b3944c55678647e2ba4a894eac9ab197
Source dataset
uspto-grants-2015_11
Patent number
US09187462B2

Reaction notes

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