Dimethylformamide → HCID 86619756, compound

Temperature

0 °C

To a 50 mL recovery flask was added 4-chloro-3-trifluoromethylphenyl isocyanate (759 mg, 3.80 mmol, 1.0 eq.) and CH3CN (8 mL). The solution was cooled to 0° C. In a separate flask was prepared a solution of N-bromophenyl-N-methylhydrazine 41 (759 mg, 3.80 mmol, 1.0 eq.) and Et3N (529 μL, 3.80 mmol, 1.0 eq.) in CH3CN (4 mL). DMF (2 mL) was added to the solution to aid in solubility of the hydrazine adduct. The solution was added to the reaction flask dropwise via syringe. After stirring for 1 h, LC/MS indicated the completion of the reaction. The reaction was concentrated and then diluted with EtOAc (100 mL). The organic phase was washed with water (50 mL) and brine (30 mL). The combined aqueous layers were extracted with EtOAc (30 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated to give a yellowish oil which later crystallized (251 mg, 16%). The crude material was used without further purification.

1. additionThe solution was added to the reaction flask dropwise via syringe
2. customthe completion of the reaction
3. concentrationThe reaction was concentrated
4. additiondiluted with EtOAc (100 mL)
5. washThe organic phase was washed with water (50 mL) and brine (30 mL)
6. extractionThe combined aqueous layers were extracted with EtOAc (30 mL)
7. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a yellowish oil which
11. customlater crystallized (251 mg, 16%)
12. customThe crude material was used without further purification

ORD record

ord-058fdeb7a0e7440f8a5d552cf3cd02e1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362017B2