Hydrochloric Acid → HCID 62025821, compound

HRID 2364362Notes

Reaction equation

HRID 2364362 reaction equation
C[O:2][CH:3](OC)[CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][S:6]1(=[O:11])=[O:10].Cl>CC(C)=O>[O:10]=[S:6]1(=[O:11])[CH2:7][CH2:8][CH2:9][N:5]1[CH2:4][CH:3]=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66223428HCID 66223428, compound

Product 1

HCID 62025821HCID 62025821, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[2,2-bis(methyloxy)ethyl]isothiazolidine 1,1-dioxide (1.00 g, 4.77 mmol) in acetone (5 mL) was added hydrochloric acid (600 μL, 1 M aqueous, 0.600 mmol). The reaction mixture was heated at 60° C. for 10 hours, then cooled to room temperature. The excess acetone was removed in vacuo and the resulting residue was partitioned between water and dichloromethane. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) provided (1,1-dioxido-2-isothiazolidinyl)acetaldehyde as a brown oil. 1H NMR (400 MHz, CDCl3) δ 9.64 (s, 1 H), 3.91 (s, 2 H), 3.39 (m, 2 H), 3.20 (t, J=7.7 Hz, 2 H), 2.44 (m, 2 H).

Workup

  1. temperaturecooled to room temperature
  2. customThe excess acetone was removed in vacuo
  3. customthe resulting residue was partitioned between water and dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-07cf44a64b884c44b280b975d8fa7d08
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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