Sodium Methoxide → HCID 68575204, compound

HRID 2111913Notes

Reaction equation

HRID 2111913 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[S:6][C:7]([CH:11]2[O:15][CH2:14][CH2:13][O:12]2)=[C:8]([Cl:10])[N:9]=1>CO>[Cl:10][C:8]1[N:9]=[C:5]([O:2][CH3:1])[S:6][C:7]=1[CH:11]1[O:15][CH2:14][CH2:13][O:12]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15665807HCID 15665807, compound

Product 1

HCID 68575204HCID 68575204, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.63 g, 11.66 mmol) is added to a solution of 2,4-dichloro-5-([1,3]dioxolan-2-yl)-thiazole (2.00 g, 8.85 mmol) in methanol (20 ml). The reaction is heated at reflux for 3.5 h, cooled, and concentrated. The residue is partitioned between aqueous saturated brine solution and ethyl acetate, separated, and the aqueous layer extracted with ethyl acetate. The ethyl acetate is dried over Na2SO4, filtered, and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 12.5% ethyl acetate/hexanes to yield (1.12 g, 93%) of 4-chloro-5-([1,3]dioxolan-2-yl)-2-methoxy-thiazole: mass spectrum (ion spray): m/z=221.9 (M+1); 1H NMR (CDCl3): δ=6.05 (1H, s), 4.15-3.97 (7H, m).

Workup

  1. temperatureThe reaction is heated
  2. temperatureat reflux for 3.5 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe residue is partitioned between aqueous saturated brine solution and ethyl acetate
  6. customseparated
  7. extractionthe aqueous layer extracted with ethyl acetate
  8. dry with materialThe ethyl acetate is dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude product is purified by flash chromatography on silica gel eluting with 12.5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3107dac6a63f44fa8ee1093cbfce1498
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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