2-Chloroethyl methyl ether → HCID 22928248, compound
Reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.Cl[CH2:8][CH2:9][O:10][CH3:11].[H-].[Na+]>CN(C=O)C.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].O>[CH3:11][O:10][CH2:9][CH2:8][N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1]Participants
8
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 2-methyl-1H-imidazole (1.0 g, 12.2 mmol) and 1-chloro-2-methoxyethane (1.34 ml, 14.62 mmol) in DMF (15 ml) was added sodium hydride (0.49 g, 12.2 mmol). The reaction mixture was heated to 80° C. for 18 hrs. The reaction mixture was transferred to a microwave vial and heated to 80° C. under microwave conditions for 1 hr. The reaction mixture was diluted with DCM (40 ml) and aq. 2M Na2CO3 (30 ml) and water (40 ml). The aqueous layer was re-extracted with DCM several times. The residue was purified by reverse phase chromatography (C18, 100% water) to afford the title compound (1.13 g, 66%).
Workup
- temperatureheated to 80° C. under microwave conditions for 1 hr
- extractionThe aqueous layer was re-extracted with DCM several times
- customThe residue was purified by reverse phase chromatography (C18, 100% water)
Sources & evidence
- ORD record
- ord-1b8dca94eac140a3b3a821e37b344abd
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409907B2
Reaction notes
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