Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-Methylbenzeneethanamine | HCID 11503 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | HCID 67139805 | HCID 67139805 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 67138505 | HCID 67138505 | — |
Reaction Steps
A solution of the title D compound, 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carboxylic acid (220 mg, 0.52 mmol) in toluene (10 mL) is treated with SOCl2 (3 mL) and the mixture is heated at 80° C. for 1 h. The volatiles are evaporated and the residue is dissolved in toluene. The solvent is evaporated again and the residue is dissolved in CH2Cl2(10 mL). A mixture of N-methylphenethylamine (35 mg, 0.25 mmol) and triethylamine (39 mg, 38.7 mmol) in CH2Cl2 (1 mL) is added and the mixture is stirred for 16 h. The solvent is evaporated and the residue is chromatographed over silica gel using 0-100% EtOAc in hexane as the eluent to afford 5-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-ylmethyl]-thiophene-2-carboxylic acid methyl-phenethyl-amide as a clear oil: [M+1]+=544.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07291635B2 |
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| Source dataset | uspto-grants-2007_11 |
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| ORD ID | ord-6470d362be734a2d9139f89b0d868856 |
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| Source note | uspto-grants-2007_11 |
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