Tert-Butanesulfinamide → HCID 88924920, compound

HRID 2279438Notes

Reaction equation

HRID 2279438 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 placed in THF (15 mL) and heated to 65° C. for 12 h. 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 concentrated. The resulting residue was purified by SiO2 chromatography (20-25% EtOAc/hexane) to afford (E)-2-methyl-N-(oxazol-5-ylmethylene)propane-2-sulfinamide (20, 1.211 g, 6.047 mmol, 58.70% yield).

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. concentrationthe organic layer was concentrated
  7. customThe resulting residue was purified by SiO2 chromatography (20-25% EtOAc/hexane)

Sources & evidence

ORD record
ord-05e6ef8847164722b766abf4113903ff
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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