Sodium hydride → 1-amino-4-chloro-1H-pyrrole-2-carbonitrile

温度

80 °C

To a rapidly stirred solution of 4-chloro-1H-pyrrole-2-carbonitrile (3.6 g, 28.4 mmol) in DMF (75 mL) was added NaH (1.7 g, 42.7 mmol) portion wise over 20 min. The dark brown solution was allowed to stir for an additional 10 min. The aminating reagent ((aminooxy)(diphenyl)phosphine oxide) (10 g, 42.7 mmol) was added in one portion. The mixture was heated to 80° C. for 6 hours. The reaction was quenched with distilled water (100 mL). EtOAc (50 mL) was added to the reaction and the solution was transferred to a separatory funnel and the organic layer was isolated while the aqueous layer was back extracted with EtOAc (2×50 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated in vacuo to yield 3.4 g of the above compound (24.02 mmol, yield 84%).

1. customThe reaction was quenched with distilled water (100 mL)
2. additionEtOAc (50 mL) was added to the reaction
3. customthe solution was transferred to a separatory funnel
4. customthe organic layer was isolated while the aqueous layer
5. extractionwas back extracted with EtOAc (2×50 mL)
6. customThe combined organic layers were collected
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo

ORDレコード

ord-760fb6000b1e441c9d53e562d3945ec0

出典データセット

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08133995B2