Isobutanesulfonyl chloride

To [2-METHYL-1-PROPANETHIOL] (200 mg, 2.22 mmol) at [0C] in acetonitrile under nitrogen was added [KNOWS] (561 mg, 5.5 mmol) then sulfuryl chloride (0.45 ml, 5.5 mmol). The reaction mixture was stirred at [0C] for 3h, diluted with [NAHCO3] and extracted with ethyl acetate. The combined organic layers were washed with brine, dried [(MGS04)] and evaporated to give the sulfonyl chloride (293 mg, 95percent)A. A. A. silyl ether from Step 1 (1.8 g, 3.2 mmol) and isobutanesulfonyl chloride (1.12g, 8 mmol) were stirred in dichloromethane (20 mL) and triethylamine (1.34 mL, 9.5 mmol) was added. After stirring at room temperature for 16h., the mixture was evaporated to dryness and the residue was partitioned between ethyl acetate and 2 M hydrochloric acid. The organic layer was collected, washed with 2 M hydrochloric acid and then 4 M sodium hydroxide, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by column chromatography (eluting with 20% ethyl acetate in hexanes) to give the sulfonamide (900 mg). This product was dissolved in dimethylformamide (6 mL) and sodium hydride (60% dispersion in mineral oil, 132 mg, 3.3 mmol) was added. The mixture was stirred at room temperature for 30 min., allyl bromide (1.1 mL, 13 mmol) was added, then the mixture was heated to 650C over 72 hrs. After cooling to room temperature and quenching with water, the mixture was extracted with ethyl acetate. The organic extract was washed with water, dried (MgSO4), filtered and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate : 80% isohexane to give the N-allyl derivative (400 mg). 1H NMR (360 MHz, CDCl3) delta 7.67 (2H, d, J 8.3 Hz), 7.52 (2H, d, J 8.3 Hz), 7.10-7.05 (2H, m), 6.85-6.79 (IH, m), 5.96-5.91 (IH, m), 5.45 (IH, d, J 17.3 Hz), 5.34 (IH, d, J 10.4 Hz), 4.22-4.09 (IH, m), 4.01-3.98 (IH, m), 3.86-3.81 (IH, m), 3.51-3.40 (2H, m), 2.88-2.63 (4H, m), 2.49-2.43 (IH, m), 2.32-2.24 (2H, m), 2.09-2.04 (IH, m), 1.95-1.72 (2H, m) and 1.11-1.03 (6H, m).

Molecular Weight:156.63
XLogP3:1.7
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:156.0011784
Monoisotopic Mass:156.0011784
Topological Polar Surface Area:42.5
Heavy Atom Count:8
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes