Hydrochloric Acid → HCID 86664425, compound
Reaction equation
[S:1](=[O:3])=[O:2].[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:16]=[C:17](N)[CH:18]=[CH:19][CH:20]=1)[CH2:9][C:8]2([CH3:23])[CH3:22].N([O-])=O.[Na+].[ClH:28]>C(O)(=O)C.O>[Cl:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:16]=[C:17]([S:1]([Cl:28])(=[O:3])=[O:2])[CH:18]=[CH:19][CH:20]=1)[CH2:9][C:8]2([CH3:23])[CH3:22]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
Sulphur dioxide was bubbled into a flask with acetic acid (10 mL) and cupric chloride (62 mg 0.63 mmol) until the green solution turned into blue. 3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (600 mg 2.09 mmol) was dissolved in a aceticacid (27 mL) and hydrochloric acid (3 mL) solution, and cooled to −10° C., sodium nitrite (213 mg, 3.09 mmol) in water (2 mL) solution was added and the mixture was stirred for 45 min. sulphur dioxide solution was added dropwise to the diazonium salt solution and stirred at −10° C. After the addition, the solution was warmed to room temperature and stirred for 24 h. The mixture was poured to 100 mL water and extracted with dichloromethane. The combined organic layers was washed with sodium bicarbonate and dried. Removal of the solvent afforded 3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-benzenesulfonyl chloride as yellow solid (crude 98 mg).
Workup
- additionAfter the addition
- temperaturethe solution was warmed to room temperature
- stirringstirred for 24 h
- extractionextracted with dichloromethane
- washThe combined organic layers was washed with sodium bicarbonate
- customdried
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-c345ced3c4f34820b81b1a861fa5833e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546427B2
Reaction notes
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