Phosphorus oxychloride → 4-Chloro-2-methylthiazolo[4,5-c]pyridine

HRID 1443105Notes

Reaction equation

HRID 1443105 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:9]=[CH:8][N+:7]([O-])=[CH:6][C:5]=2[N:11]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[C:5]2[N:11]=[C:2]([CH3:1])[S:3][C:4]=2[CH:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 685381222-Methyl-thiazolo[4,5-c]pyridine 5-oxide

Product 1

HCID 768504734-Chloro-2-methylthiazolo[4,5-c]pyridine

Procedure

2-Methyl-thiazolo[4,5-c]pyridine 5-oxide (230 mg, 1.38 mmol) was refluxed 2 hrs in 4 ml of phosphoryl chloride. The reaction mixture was evaporated and extracted with ethyl acetate and saturated sodium bicarbonate-solution. The organic extracts were dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient). The desired product was obtained as a light yellow solid (180 mg, 70%), MS: m/e=185.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with ethyl acetate and saturated sodium bicarbonate-solution
  3. dry with materialThe organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 90:10->0:100 gradient)

Sources & evidence

ORD record
ord-72bdcada229f40468e041e2b49dc8796
Source dataset
uspto-grants-2010_02
Patent number
US07659401B2

Reaction notes

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