5-Nitrosalicylic acid → HCID 4561570, compound

Thionyl chloride (20 ml) was added to 5-nitrosalicylic acid (5 g). The mixture was heated under reflux for 2 hr. Thionyl chloride was removed by distillation under the reduced pressure. Toluene was added to the residue, and the mixture was concentrated. This procedure was repeated twice. The residue was dissolved in methylene chloride (40 ml). Cyclohexylamine (9.4 ml) was added under ice cooling to the solution. The mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate. The diluted solution was washed with water, dilute hydrochloric acid, and water in that order, and then dried over magnesium sulfate. The solvent was then removed by distillation under the reduced pressure to give 6.9 g of N-cyclohexyl-5-nitrosalicylamide.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 2 hr
3. customThionyl chloride was removed by distillation under the reduced pressure
4. additionToluene was added to the residue
5. concentrationthe mixture was concentrated
6. dissolutionThe residue was dissolved in methylene chloride (40 ml)
7. additionCyclohexylamine (9.4 ml) was added under ice cooling to the solution
8. additionThe reaction solution was diluted with ethyl acetate
9. washThe diluted solution was washed with water, dilute hydrochloric acid, and water in that order
10. dry with materialdried over magnesium sulfate
11. customThe solvent was then removed by distillation under the reduced pressure

ORD record

ord-fcb6ca89a38a4b4e95433121de23cb7b

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583144B2