Dimethylformamide → HCID 963338, compound

To a slurry of furan-2-carboxylic acid (10.0 g, 89 mmol) in 100 mL DCM at 0° C. under nitrogen was added DMF (0.069 ml, 0.89 mmol) and oxalyl chloride (9.9 ml, 112 mmol) slowly in small portions over 5 min. The reaction was allowed to warm to ambient temperature. After 3 h, the clear solution was concentrated in vacuo and the resulting oil was dissolved in 75 mL THF and cooled to 0° C. A solution of tert-butylamine (28 ml, 268 mmol) in 25 mL THF was added dropwise over 1 h. The bath was allowed to expire and the slurry was stirred over the weekend. The reaction was concentrated in vacuo and partitioned between 1N NaOH and DCM. The aqueous layer was extracted twice with DCM. The combined organic layers were concentrated in vacuo to give N-tert-butylfuran-2-carboxamide as a white solid. MS m/z=168 [M+H]+. Calc'd for C9H13NO2: 167.2.

1. concentrationthe clear solution was concentrated in vacuo
2. dissolutionthe resulting oil was dissolved in 75 mL THF
3. temperaturecooled to 0° C
4. concentrationThe reaction was concentrated in vacuo
5. custompartitioned between 1N NaOH and DCM
6. extractionThe aqueous layer was extracted twice with DCM
7. concentrationThe combined organic layers were concentrated in vacuo

ORD record

ord-77b4fefbb43d4cd9a44041a9a674620d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686155B2