Benzoic Acid → HCID 178527945, compound

Temperature

80 °C

Phosphorus oxychloride (7 ml) was added to 3.67 g (30 mmol) of benzoic acid and 2.73 g (30 mmol) of thiosemicarbazide, and the mixture was stirred at 80° C. for one hr. The reaction solution was added dropwise to 500 ml of a saturated aqueous sodium hydrogencarbonate solution. The resultant precipitate was collected by filtration and was dried. The dried precipitate was suspended in 20 ml of acetonitrile. Cupric chloride (6 g, 45 mmol) and 5.3 g (45 mmol) of tert-butyl nitrite were added to the suspension, and the mixture was stirred at room temperature for 3 hr. The solvent was removed by distillation. Ethyl acetate (100 ml) was added to the residue, and the mixture was washed with 30 ml of 1 N hydrochloric acid and 50 ml of distilled water in that order. The solvent was removed by distillation. The residue was dissolved in 20 ml of ethanol, 3.4 g (45 mmol) of thiourea was added to the solution, and the mixture was heated under reflux for 3 hr. The solvent was removed by distillation, 100 ml of ethyl acetate was added to the residue, and the mixture was washed with 50 ml of distilled water. The solvent was removed by distillation, and the residue was then purified by column chromatography on silica gel (chloroform:methanol=30:1) to give 3.17 g (yield 55%) of the title compound.

1. filtrationThe resultant precipitate was collected by filtration
2. customwas dried
3. stirringthe mixture was stirred at room temperature for 3 hr
4. customThe solvent was removed by distillation
5. additionEthyl acetate (100 ml) was added to the residue
6. washthe mixture was washed with 30 ml of 1 N hydrochloric acid and 50 ml of distilled water in that order
7. customThe solvent was removed by distillation
8. dissolutionThe residue was dissolved in 20 ml of ethanol
9. temperaturethe mixture was heated
10. temperatureunder reflux for 3 hr
11. customThe solvent was removed by distillation, 100 ml of ethyl acetate
12. additionwas added to the residue
13. washthe mixture was washed with 50 ml of distilled water
14. customThe solvent was removed by distillation
15. customthe residue was then purified by column chromatography on silica gel (chloroform:methanol=30:1)

ORD record

ord-d13f465a719948f79d2dfa51470835f2

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07871982B2