Hydrochloric Acid → 4-Chloro-2-methoxy-1,3-thiazole-5-carbaldehyde

HRID 2111914Notes

Reaction equation

HRID 2111914 reaction equation
Cl.[Cl:2][C:3]1[N:4]=[C:5]([O:13][CH3:14])[S:6][C:7]=1[CH:8]1OCC[O:9]1.[OH-].[Na+]>O1CCCC1>[Cl:2][C:3]1[N:4]=[C:5]([O:13][CH3:14])[S:6][C:7]=1[CH:8]=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68575204HCID 68575204, compound

Product 1

HCID 337778854-Chloro-2-methoxy-1,3-thiazole-5-carbaldehydeYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5N HCl (10 ml) is added to a solution of 4-chloro-5-([1,3]dioxolan-2-yl)-2-methoxy-thiazole (1.80 g, 8.13 mmol) in tetrahydrofuran (50 ml). After 1 h, the reaction is poured into 2N NaOH (100 ml) and extracted with ethyl acetate (3×100 ml). The ethyl acetate is washed with aqueous saturated brine solution, dried with anhydrous Na2SO4, filtered, and concentrated. The crude product is purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes to yield (1.30 g, 90%) of 4-chloro-2-methoxy-thiazole-5-carboxaldehyde: mass spectrum (ion spray): m/z=178.0 (M+1); 1H NMR (CDCl3): δ=9.95 (1H, s), 4.22 (3H, s).

Workup

  1. extractionextracted with ethyl acetate (3×100 ml)
  2. washThe ethyl acetate is washed with aqueous saturated brine solution
  3. dry with materialdried with anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by flash chromatography on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-e3ada45f49b642ab8322b0683da3c16d
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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