Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Chlorosuccinimide | HCID 31398 | — |
| Reactant | HCID 68699037 | HCID 68699037 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68697358 | HCID 68697358 | 28% |
Reaction Steps
2-Amino-N-(4-tert-butyl-benzyl)-5-methyl-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide (60 mg, 0.128 mmol) was dissolved in acetonitrile (2 ml) and N-chlorosuccinimide (23 mg, 0.128 mmol) was added. The reaction was heated to 95° C. for 4 h. The reaction mixture was cooled to RT and partitionated between water and methylene chloride. The aqueous layer was extracted with methylene chloride and the combined organic phase was dried (MgSO4), filtered and concentrated in vacuo to give a residue which was purified by flash column chromatography (heptane/ethyl acetate 7:3) to yield the desired product (18 mg, 28%) as a brown gum. MS (ISP) 503.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07678818B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-d1f7198c026f40a592cad70f73ee04d3 |
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| Source note | uspto-grants-2010_03 |
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