Chloroacetyl isocyanate → HCID 14456841, compound

HRID 1649764Notes

Reaction equation

HRID 1649764 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[N:10]=1.[Cl:14][CH2:15][C:16]([N:18]=[C:19]=[O:20])=[O:17]>ClCCl.CN(C)C=O.C(N(CC)CC)C>[Cl:14][CH2:15][C:16]([NH:18][C:19]([O:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[N:10]=1)=[O:20])=[O:17]

Participants

6

Reactant 2

HCID 78209Chloroacetyl isocyanateHCID 19854391HCID 19854391, compound

Product 1

HCID 14456841HCID 14456841, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

In a mixture of 30 ml of dichloromethane and 10 ml of dimethylformamide is dissolved 500 mg of 6-(2-hydroxyethylthio)imidazo[1,2-b]pyridazine, followed by addition of 2 drops of triethylamine. Then, with stirring and cooling at -20° C., 490 mg of chloroacetyl isocyanate is added dropwise. Thereafter, the mixture is stirred at -20° to -10° C. for 1 hour. The dichloromethane is distilled off under reduced pressure and the residual solution is subjected to silica gel (100 g) column chromatography, with elution being carried out with ethyl acetate. The eluate is concentrated under reduced pressure. To the solid residue is added 5 ml of water and after stirring, the crystals are collected by filtration. The crystals are washed with 5 ml each of water and ether and dried. The above procedure yields 6-[2-(N-chloroacetylcarbamoyloxy)ethylthio]imidazo[1,2-b]pyridazine as crystals melting at 190° to 195° C.

Workup

  1. stirringThereafter, the mixture is stirred at -20° to -10° C. for 1 hour
  2. distillationThe dichloromethane is distilled off under reduced pressure
  3. washthe residual solution is subjected to silica gel (100 g) column chromatography, with elution
  4. concentrationThe eluate is concentrated under reduced pressure
  5. additionTo the solid residue is added 5 ml of water
  6. stirringafter stirring
  7. filtrationthe crystals are collected by filtration
  8. washThe crystals are washed with 5 ml each of water and ether
  9. customdried

Sources & evidence

ORD record
ord-35d0385d6ff541e2a5da8db7315494d0
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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