Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | 5-(tetrahydrofuran-2-yl)-1,3,4-thiadiazol-2-amine | HCID 4085892 | — |
| Reactant | Sodium Nitrite | HCID 23668193 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 63384188 | HCID 63384188 | — |
Reaction Steps
To 5-(Tetrahydro-furan-2-yl)-[1,3,4]thiadiazol-2-ylamine (0.5 g, 2.9 mmol) was added 48% HBr (7 ml) and H2O (7 ml). The reaction mixture was cooled to 0° C. using an icebath. Cu(I)Br (0.42 g, 2.9 mmol) was added, followed by a the dropwise addition of solution of NaNO2 (0.48 g, 10 mmol) in H2O (18 ml). The reaction mixture was stirred for a further 10 mins at 0° C. then allowed to warm up to room temperature over a 35 min period. A solution of saturated bicarbonated was added to the reaction mixture until the pH=6, then extracted with EtOAc, dried (MgSO4), filtered and the solvent removed in vacuo to afford the product (0.5 g, 2.1 mmol). MS: [M+H]+235, 237.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796244B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-d0f0ef69494245f98bbd13a79987427b |
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| Source note | uspto-grants-2014_08 |
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