Buchwald–Hartwig amination: Iodobenzene → 4-methoxy-N-phenylbenzo[d]thiazol-2-amine
15% yield, run at 90 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | Iodobenzene | C₆H₅I | |
| Reactant | 4-Methoxy-2-aminobenzothiazole | C₈H₈N₂OS | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-methoxy-N-phenylbenzo[d]thiazol-2-amine | C₁₄H₁₂N₂OS | 15.22% |
Conditions
- Temperature
- 90 °C
Yield
- 15% of 4-methoxy-N-phenylbenzo[d]thiazol-2-amine.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
4-methoxybenzo[d]thiazol-2-amine (0.216 g, 1.20 mmol), iodobenzene (0.112 mL, 1.00 mmol), XANTPHOS (0.058 g, 0.10 mmol), Pd2(dba)3 (0.027 g, 0.03 mmol) and SODIUM TERT-BUTOXIDE (0.192 g, 2.00 mmol) placed in a sealed reaction via under an atmosphere of nitrogen and heated at 90ºC for 1 hour. LC/MS indicated mainly product, little SM. Cooled, diluted DCM and washed with water and brine. Org phase dried/MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, eluting with dichloromethane. Pure fractions were evaporated to dryness to afford 4-methoxy-N- phenylbenzo[d]thiazol-2-amine (0.039 g, 15.22 %) as an colorless solid. EN01327-44-1 (0.039 g, 0.15 mmol, 15.22 %) Not sure why yield so low, crude lc/ms looked fine. Reaction left for several days before
The source
This record comes from experimental reaction archive (ord-0eb7fc5c164b43bc9a05a46e98a37b12). Open the source and check it against what is on this page.
experimental reaction archive record ord-0eb7fc5c164b43bc9a05a46e98a37b12 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
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Where to next
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