1-Bromo-2-Chloroethane → HCID 178478507, compound
Reaction equation
[OH:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1.Br[CH2:37][CH2:38][Cl:39]>C(#N)C>[Cl:39][CH2:38][CH2:37][O:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Hydroxy-3-(2-thienyl)pyrazole (2.49 g), potassium carbonate (3.11 g) and 18-crown-6-ether (0.13 g) is suspended in acetonitrile (31 ml), to which 1-bromo-2-chloroethane (2.15 g) is added drop by drop and the reaction mixture is refluxed for 5 hours by heating. After the reaction is completed, it is extracted with ethyl acetate, washed with aqueous solution of sodium hydrogen carbonate and dried with anhydrous magnesium sulfate. Dichloromethane is added to the residue obtained by distilling off ethyl acetate and the insoluble matter is filtered off. Dichloromethane is added and distilled off to obtain the objective 5-(2-chloroethoxy)-3-(2-thienyl)pyrazole (1.0 g). mp. 134-138° C.
Workup
- additionis added drop by drop
- temperaturethe reaction mixture is refluxed for 5 hours
- temperatureby heating
- extractionit is extracted with ethyl acetate
- washwashed with aqueous solution of sodium hydrogen carbonate
- dry with materialdried with anhydrous magnesium sulfate
- additionDichloromethane is added to the residue
- customobtained
- distillationby distilling off ethyl acetate
- filtrationthe insoluble matter is filtered off
- additionDichloromethane is added
- distillationdistilled off
Sources & evidence
- ORD record
- ord-c8a0e7acfc5d4afe9a7d5fba79538d68
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06593358B1
Reaction notes
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