2,4-Dichloro-5-(1,3-dioxolan-2-yl)-1,3-thiazole → HCID 22147870, compound

HRID 2111930Notes

Reaction equation

HRID 2111930 reaction equation
C([Li])CCC.Cl[C:7]1[S:8][C:9]([CH:13]2[O:17][CH2:16][CH2:15][O:14]2)=[C:10]([Cl:12])[N:11]=1>O1CCCC1>[Cl:12][C:10]1[N:11]=[CH:7][S:8][C:9]=1[CH:13]1[O:17][CH2:16][CH2:15][O:14]1

Participants

4

Reactant 2

HCID 156658072,4-Dichloro-5-(1,3-dioxolan-2-yl)-1,3-thiazoleHCID 178418339Butyllithium

Product 1

HCID 22147870HCID 22147870, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Slowly add n-butyllithium (2.5 M in hexanes, 44.0 mL, 110 mmol) to a stirred solution of 2,4-dichloro-5-[1,3]dioxolan-2-yl-thiazole (19.33 g, 85.5 mmol) and anhydrous tetrahydrofuran (400 mL) at −78° C. under nitrogen. Stir for 1.5 h at −78° C. and then quench with water and pour the reaction into brine (300 mL). Extract with ethyl acetate (3×200 mL), dry over sodium sulfate, and filter off the sodium sulfate. Concentrate on a rotary evaporator and purify the crude product by flash chromatography on silica gel eluting with 25% ethyl acetate/hexanes to yield 15.27 g (93%) of 4-chloro-5-[1,3]dioxolan-2-yl-thiazole: mass spectrum (ion spray): m/z=192.0 (M+1); 1H NMR (CDCl3): δ=8.75 (s, 1H), 6.18 (s, 1H), 4.22-4.04 (m, 4H).

Workup

  1. customat −78° C.
  2. customquench with water
  3. additionpour
  4. customthe reaction into brine (300 mL)
  5. extractionExtract with ethyl acetate (3×200 mL)
  6. dry with materialdry over sodium sulfate
  7. filtrationfilter off the sodium sulfate
  8. concentrationConcentrate on a rotary evaporator
  9. custompurify the crude product by flash chromatography on silica gel eluting with 25% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d5d4c16341d84643b98f2fe3a977033f
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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