1,1-Dichloroethane → 5,7-Dichloroimidazo[5,1-b]thiazole
Reaction equation
[S:1]1C=C[N:3]2[CH:6]=[N:7][CH:8]=[C:2]12.[Cl:9]N1C(=O)CCC1=O.[Cl:17][CH:18](Cl)[CH3:19]>C(OCC)(=O)C>[Cl:9][C:6]1[N:7]2[C:19]([S:1][CH:2]=[CH:8]2)=[C:18]([Cl:17])[N:3]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 62.5 °C
Procedure
To a solution of imidazo[5,1-b]thiazole (18.624 g) in dichloroethane (450 ml) was added 20.030 g of N-chlorosuccinimide, the mixture was heated in a bath at a temperature of 60-65° C. for 1 hour. After air cooling, insolubles were removed by filtration, and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in 3.0 l of ethyl acetate, and washed three times with 3.0 l of distilled water. After the organic layer was dried over anhydrous magnesium sulfate and the magnesium sulfate was removed by filtration, the solvent was removed under reduced pressure. The solid product thus obtained was purified by column chromatography on silica gel (ethyl acetate) to give 2.020 g of 5,7-dichloroimidazo[5,1-b]thiazole as a pale brown powder from the fraction of Rf=0.85.
Workup
- temperatureAfter air cooling
- custominsolubles were removed by filtration
- customthe solvent was removed under reduced pressure
- customThe residue thus obtained
- washwashed three times with 3.0 l of distilled water
- dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
- customthe magnesium sulfate was removed by filtration
- customthe solvent was removed under reduced pressure
- customThe solid product thus obtained
- customwas purified by column chromatography on silica gel (ethyl acetate)
Sources & evidence
- ORD record
- ord-62e45004e1aa4590be9e0353dc9dab15
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310056B1
Reaction notes
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