Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Methylhexanedioic acid | HCID 12292 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Thiosemicarbazide | HCID 2723789 | — |
| Solvent | Phosphorus oxychloride | HCID 24813 | — |
| Product | HCID 86687865 | HCID 86687865 | 106.3% |
Reaction Steps
A mixture of 3-methyl adipic acid (5.00 g, 31.22 mmol) and thiosemicarbazide (5.69 g, 62.43 mmol) in POCl3 (45 mL) was heated at 90° C. for 4 h. The reaction was cooled to room temperature and poured into a mixture of ice and water. Sodium hydroxide pellets were added to the mixture until it was basic (pH 14). The white precipitate was collected by suction filtration, rinsed with water and dried to provide 5,5′-(2-methylbutane-1,4-diyl)-bis(1,3,4-thiadiazol-2-amine) (1003, 8.97 g). 1H NMR (300 MHz, DMSO-d6) δ 7.00 (s, 4H), 2.89-2.81 (m, 3H), 2.89-2.81 (m, 3H), 2.69 (dd, J=7.6, 7.6 Hz, 1H), 1.89-1.46 (m, 3H), 0.94 (d, J=6.6 Hz, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08865718B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-03096fed6af24ef093d72de8c97312bf |
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| Source note | uspto-grants-2014_10 |
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