Hydrochloric Acid → HCID 89536859, compound
Reaction equation
[ClH:1].N[C:3]1[C:11]([S:12][CH3:13])=[CH:10][C:9]([CH3:14])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].N([O-])=O.[Na+]>O.[Cu]Cl>[Cl:1][C:3]1[C:11]([S:12][CH3:13])=[CH:10][C:9]([CH3:14])=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
13 ml of concentrated hydrochloric acid were added to 6.00 g (30.4 mmol) of 2-amino-5-methyl-3-(methylthio)benzoic acid in 35 ml of water, and the mixture was heated at 60° C. for a few minutes. The solution was then cooled to a temperature of 0° C.-5° C., and a solution of 2.31 g (33.5 mmol) of sodium nitrite in 10 ml of water was slowly added dropwise at this temperature. The mixture was subsequently stirred at this temperature for another 1 h. This solution was added dropwise to a mixture, at RT, of 4.52 g (45.6 mmol) of copper(I) chloride, 35 ml of water and 27 ml of concentrated hydrochloric acid. The mixture was stirred at room temperature for 15 minutes and then slowly heated to reflux temperature. The contents were then heated under reflux for 15 minutes. For work-up, the reaction mixture was cooled and filtered, and the residue was washed with water. This gave 5.62 g of 2-chloro-5-methyl-3-(methylthio)benzoic acid as residue.
Workup
- temperatureThe solution was then cooled to a temperature of 0° C.-5° C.
- stirringThe mixture was stirred at room temperature for 15 minutes
- temperatureslowly heated
- temperatureto reflux temperature
- temperatureThe contents were then heated
- temperatureunder reflux for 15 minutes
- temperatureFor work-up, the reaction mixture was cooled
- filtrationfiltered
- washthe residue was washed with water
Sources & evidence
- ORD record
- ord-700e3b95eb1e4057ba632ec9583d7965
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09259001B2
Reaction notes
Loading…