Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Chloroacetonitrile | HCID 7856 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 69967088 | HCID 69967088 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 10143559 | HCID 10143559 | 83.8% |
Reaction Steps
A mixture of 250 mg (0.50 mmol) of (2-chloro-3,4-dimethoxyphenyl)-N-(4,5-dimethylimidazol-2-yl)methyl-N-(3-methylbutyl)carboxamide, 52 μL of chloroacetonitrile (0.75 mmol), 276 mg (2.0 mmol) of K2CO3, and 3 mL of anhydrous DMF is stirred under nitrogen at 22° C. for 24 h and poured into 10% NaCl. The mixture is extracted with 20 mL of ethyl acetate. The extract is concentrated under reduced pressure, diluted with 20 mL of xylenes, and the volatiles are thoroughly evaporated. The crude product is purified by chromatography on 30 g of silica gel using chloroform—methanol—28% ammonium hydroxide (98:1.8:0.2, v/v/v) for elution to afford 113 mg (42% yield) of the title compound. Mass Spec m/z (M++1) 539.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06509366B2 |
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| Source dataset | uspto-grants-2003_01 |
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| ORD ID | ord-5538d297ad904fafa9aa317f41d0d00a |
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| Source note | uspto-grants-2003_01 |
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