Thionyl Chloride → HCID 43620016, compound

HRID 1774773Notes

Reaction equation

HRID 1774773 reaction equation
[O:1]=[S:2]1(=[O:10])[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8]O.O=S(Cl)[Cl:13].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:13][CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][S:2]1(=[O:10])=[O:1]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 436200851157045-79-8

Product 1

HCID 43620016HCID 43620016, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 2-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-ethanol (0.14 g, 0.847 mmol) in DCM (4 mL) was added SOCl2 (0.151 g, 1.27 mmol) and the reaction mixture was heated to 40° C. for 2 h. The mixture was cooled to room temperature, diluted with DCM, poured into a sat. NaHCO3 solution (10 mL) and the aqueous layer was extracted with DCM (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.046 g, 30%) as an orange oil which was used with no further purification. MS: 184.1 (M+H+).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe aqueous layer was extracted with DCM (2×20 mL)
  3. dry with materialCombined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-b3357f9e8b9c47ffbc75a78debee8ec8
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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