Water → 2-Acetyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-7-sulfonyl Chloride
Reaction equation
[CH3:1][C:2]1([CH3:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][N:4]([C:12](=[O:14])[CH3:13])[CH2:3]1.[Cl:16][S:17](O)(=[O:19])=[O:18].O>ClCCl>[C:12]([N:4]1[CH2:3][C:2]([CH3:15])([CH3:1])[C:11]2[C:6](=[CH:7][C:8]([S:17]([Cl:16])(=[O:19])=[O:18])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:14])[CH3:13]Participants
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(4,4-dimethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone (D2) (0.5 g, 2.5 mmol) in dry dichloromethane (2 ml) was added over 15 minutes to an ice-cooled, stirred solution of chlorosulfonic acid (1.7 ml, 25 mmol) in dry dichloromethane (6 ml). After stirring the solution at 0° C. for 1 h, it was warmed to ambient temperature and stirred for a further 3 h. The solution was then carefully poured onto a mixture of ice (30 g) and water (30 ml) with stirring. The layers were separated and the aqueous layer was extracted with dichloromethane (30 ml). The combined organic layers were dried (MgSO4) and concentrated in vacuo to an oil which was stirred at room temperature for 15 minutes with diethyl ether (30 ml) to afford the title compound (D3) as a white solid (0.21 g, 27%), δH (CDCl3, rotamers observed)/ppm 1.33, 1.37 (6H, 2×s), 2.21, 2.24 (3H, 2×s), 3.47, 3.66 (2H, 2×s), 4.77, 4.88 (2H, 2×s), 7.55-7.62 (1H, m), 7.77-7.90 (2H, m).
Workup
- temperaturecooled
- temperatureit was warmed to ambient temperature
- stirringstirred for a further 3 h
- stirringwith stirring
- customThe layers were separated
- extractionthe aqueous layer was extracted with dichloromethane (30 ml)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated in vacuo to an oil which
- stirringwas stirred at room temperature for 15 minutes with diethyl ether (30 ml)
Sources & evidence
- ORD record
- ord-2ae70050139543bd8753008615192cd8
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849644B2
Reaction notes
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