Sulfuryl chloride → 3-Chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-amine

HRID 1653958Notes

Reaction equation

HRID 1653958 reaction equation
S(Cl)([Cl:4])(=O)=O.[NH2:6][C:7]1[CH:15]=[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][N:9]2[N:8]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[NH2:6][C:7]1[C:15]([Cl:4])=[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][N:9]2[N:8]=1

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 543166624,5,6,7-Tetrahydropyrazolo[1,5-a]pyridin-2-amine

Product 1

HCID 229128053-Chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 g (37 mmol) sulfuryl chloride was added dropwise to 5.08 g (37 mmol) 2-amino-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine, dissolved in 30 ml methylene chloride, with ice-cooling. The mixture was stirred for 1 hour, then added to saturated aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated. Purification was carried out by silica gel column chromatography to ethyl acetate/hexane).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-625fa882c6e247268f0696a5836513c5
Source dataset
uspto-grants-1995_04
Patent number
US05405829

Reaction notes

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