Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzaldehyde | HCID 240 | — |
| Reactant | Carbonate Ion | HCID 19660 | — |
| Reactant | Carbodiimide | HCID 160435 | — |
| Reactant | Triethylammonium | HCID 1385867 | — |
| Reactant | 5-Chloro-2-picolinic acid | HCID 2762872 | — |
| Reactant | HCID 58504252 | HCID 58504252 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Product | HCID 58504128 | HCID 58504128 | 39.6% |
Reaction Steps
A mixture of 5-chloropicolinic acid (43 mg) and N-cyclohexylcarbodiimide-N′-propyloxymethyl polystyrene resin (PS-Carbodiimide: Argonaut Technologies catalog number 80,037-1; 354 mg) in dichloroethane (4 mL) was shaken for 45 minutes. The reaction was shaken for 45 minutes more after the addition of N,N-dimethylformamide (0.1 mL). The compound prepared in Example 9 (50 mg) was added and the mixture was shaken overnight. Benzaldehyde polystyrene resin (PS-benzaldehyde: Argonaut Technologies catalog number 80,036-2; 184 mg) was then added and the reaction was shaken for 3.5 hours. Macroporous triethylammonium methylpolystyrene carbonate (MP-carbonate: Argonaut Technologies catalog number 80,026-9; 202 mg) was added and the reaction was shaken for 1.5 hours more. The mixture was then filtered and concentrated to obtain the title compound (30 mg) having the following physical data.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08809538B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-275fab5412d248d3990b3b2d05ac79ae |
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| Source note | uspto-grants-2014_08 |
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