Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Pentanethiol | HCID 8067 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | sodium thiosulfate NaHCO3 | HCID 22607107 | — |
| Reactant | N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine | HCID 86653112 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 86653124 | HCID 86653124 | 18.3% |
Reaction Steps
To a solution of N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.3 g, 0.80 mmol, 1 eq.) in 2 ml of NMP were added 1-pentanethiol (0.084 g, 0.80 mmol, 1 eq.), Cs2CO3 (0.262 g, 0.80 mmol, 1 eq.). The reaction was microwaved (30 sec prestirring, abs-normal, fixed-hold) 120° C. for 60 s. Then a mixture water/EtOAc (1/1) was added and the aqueous layer was separated and extracted with EtOAc. The organics were combined, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give 1-(1-methyl-1H-tetrazol-5-yl)-N-{[6-(pentylsulfanyl)pyridin-2-yl]methoxy}-1-phenylmethanimine (0.058 g, 17% yield) as a viscous oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08466176B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-d38a4f9c34404545bb939b005f1abd41 |
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| Source note | uspto-grants-2013_06 |
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