Chloroacetyl chloride → 5-(Chloromethyl)-3-(thiazol-2-yl)-1,2,4-oxadiazole
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].O[NH:7][C:8]([C:10]1[S:11][CH:12]=[CH:13][N:14]=1)=[NH:9].C([O-])([O-])=O.[K+].[K+]>O>[Cl:1][CH2:2][C:3]1[O:4][N:9]=[C:8]([C:10]2[S:11][CH:12]=[CH:13][N:14]=2)[N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
Chloroacetyl Chloride (5.0 mL, 44.5 mmol) was added to N-Hydroxy-thiazole-2-carboxamidine (0.50 g, 3.49 mmol) and K2CO3 (1.0 g, 7.20 mmol). The reaction mixture was heated at 100° C. for 15 min. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (230-400 M, 10% EtOAc-Hexane) to get the desired product (0.18 g, 25%) as a white solid.
Workup
- extractionextracted with ethyl acetate (3×50 mL)
- washThe combined organics was washed with water, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe crude residue was purified over silica gel (230-400 M, 10% EtOAc-Hexane)
Sources & evidence
- ORD record
- ord-0320befdb85141d589ac44fe8574baa9
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088791B2
Reaction notes
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