Dimethylcarbamoyl Chloride → HCID 86640304, compound

Temperature

0 °C

To a stirred solution of 1H-indole-5-carbaldehyde (0.87 g, 6 mmol) in anhydrous DMF (10 mL) was added sodium hydride (60% dispersion in mineral oil, 0.36 g, 9 mmol) portionwise at 0° C. under argon. The reaction mixture was stirred at 0° C. for 10 min and rt for 20 min before dimethylcarbamic chloride was added dropwise at 0° C. After the reaction mixture was stirred at 0° C. for 10 min and rt for 2 hr, saturated ammonium chloride aqueous solution (10 mL) was added to quench the reaction. The reaction mixture was concentrated, diluted with water (10 mL) and extracted with dichloromethane (20 mL). The dichloromethane extract was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave 5-formyl-N,N-dimethyl-1H-indole-1-carboxamide (1.3 g, 5.8 mmol, 97% yield) as a white solid, the NMR spectrum of which was consistent with the desired structure.

1. additionwas added dropwise at 0° C
2. customto quench
3. customthe reaction
4. concentrationThe reaction mixture was concentrated
5. additiondiluted with water (10 mL)
6. extractionextracted with dichloromethane (20 mL)
7. extractionThe dichloromethane extract
8. dry with materialwas dried (Na2SO4)
9. concentrationconcentrated

ORD record

ord-b9234ae3800340b0a0d6d03fdf542e07

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08067447B2