1-Chloro-5-isoquinolinesulfonyl Chloride

Off-White Solid

Chlorosulfonic acid (40 mL) is added slowly to 1-chloro-isoquinoline (9.92 g, 60.6 mmol) at 0 °C with stirring under nitrogen. The resultant mixture is heated at 155 °C for 24 hours. Then the mixture is cooled to ambient temperature before it is poured very slowly into ice (200 g). While cold, the mixture is extracted with dichloromethane (300 mL). The organic layer is dried over NA2SO4, filtered and concentrated IN VACUA to give 13.6 g (51. 9 mmol, yield 86percent) of 1-chloro-isoquinoline-5-sulfonyl chloride as a white powder. 1H NMR (CDC13) : S7. 87 (t, J = 7.5 Hz, 1H), 8.52 (d, J = 6.2 Hz, 1H), 8.59 (d, J = 6. 2 Hz, 1H), 8.62 (d, J = 7.5 Hz, 1H), 8.82 (d, J = 7.5 Hz, 1H). Powdered 1-CHLORO-ISOQUINOLINE-5-SULFONYL chloride (10.0 g, 38.2 mmol) is added in portions to a stirred solution of (2-amino-ethyl) -carbamic acid tert-butyl ester (7.33 g, 45. 8 mmol) and NEt3 (10.7 mL, 76.4 mmol) in anhydrous CH2C12 (200 mL) at 0 °C under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 4 hours. The mixture is concentrated and chromatographed on silica gel (gradient 0-5percent CH30H in CH2Cl2) to give 13. 8 g (35.8 mmol, 94percent yield) of the title compound as foam. ESIMS: M/Z 386 [(M+H) +, 35C1], 388 [(M+H)+, 37Cl]. Analysis for C16H20CIN304S : calcd: C, 49.80 ; H, 5.22 ; N, 10.89 ; found: C, 49.70 ; H, 5.22 ; N, 10.72.

Molecular Weight:262.11
XLogP3:3.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:260.9418050
Monoisotopic Mass:260.9418050
Topological Polar Surface Area:55.4
Heavy Atom Count:15
Complexity:328
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes