Thionyl Chloride → HCID 319582, compound

HRID 1799593Notes

Reaction equation

HRID 1799593 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][CH:3]=1.[S:10](Cl)(Cl)=O>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[N:8][S:10][N:9]=2)[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 106306156-Chloropyridine-2,3-diamine

Product 1

HCID 319582HCID 319582, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

6-Chloropyridine-2,3-diamine (Example 23, Step 1) (150 mg, 1.045 mmol) was taken-up in dioxane (21.0 ml) under argon at room temperature. Thionyl chloride (686 μl, 9.40 mmol) was added dropwise over 15 minutes. The mixture was then stirred at 75° C. for 24 hours. The reaction was quenched with water and extracted three times with ethyl acetate. All organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes) to afford 5-chloro[1,2,5]thiadiazolo[3,4-b]pyridine. LRMS (APCI) calc'd for (C5H3ClN3S) [M+H]+, 172. found 172.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe resulting crude product was purified by silica gel chromatography (0-65% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c2ce3ba9dc7f4319a92798bb4806793d
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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