3-Chloropropionyl chloride → HCID 22989399, compound

HRID 1169028Notes

Reaction equation

HRID 1169028 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][N:10]=2)[N:7]=1.[Cl:11][CH2:12][CH2:13][C:14](Cl)=[O:15]>CN(C)C(=O)C>[Cl:11][CH2:12][CH2:13][C:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([N:8]=[CH:9][N:10]=2)[N:7]=1)=[O:15]

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 12242060HCID 12242060, compound

Product 1

HCID 22989399HCID 22989399, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

6-Amino[1,2,4]triazolo[1,5-b]pyridazine (0.80 g) was dissolved in N,N-dimethylacetamide (7 ml), followed by addition of 3-chloropropionyl chloride (0.68 ml) under ice-cooling. The mixture was stirred at room temperature for 1 hour and poured into ice-water, followed by extraction with a mixture of ethyl acetate and tetrahydrofuran (1:1). The extract was washed with an aqueous sodium chloride saturated solution, dried over magnesium sulfate and concentrated under reduced pressure. Ethyl ether was added to the residue. The resulting crystals were collected by filtration and dried to yield the title compound (0.875 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with a mixture of ethyl acetate and tetrahydrofuran (1:1)
  3. washThe extract was washed with an aqueous sodium chloride saturated solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionEthyl ether was added to the residue
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-11f49fb21b77433da1657fcc5324d332
Source dataset
uspto-grants-2003_09
Patent number
US06627630B1

Reaction notes

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