2-chloroethane-1-sulfonyl chloride (Lancaster)
DCM (Dry)
4-Methyl-benzylamine (Avocado)
Triethylamine (Avocado)

To a stirring solution of 2-chloroethane-1-sulfonyl chloride (10 g, 61.34 mmol) in DCM (100 mL) at -15^oC, was added dropwise a premixed suspension of 4-methyl-benzyl amine (8.2 g, 67.48 mmol) and NEt₃ (12.4 g, 122.68 mmol) in DCM (25 mL). The reaction mixture was left to stir for a further 30 minutes after addition, and then left to warm to RT. The reaction was diluted with more DCM (50-60 mL) and washed with 2M HCl (3 x 80 mL), H₂O (1 x 80 mL), dried (MgSO₄), and filtered. The filtrate collected was concentrated in vacuo to give the crude which was purified by flash chromatography (starting 3:1 Petroleum ether 40-60°C/Et₂O) to furnish the desired product (11.7 g, 90%) as white crystals.

CAUTION: The reaction is exothermic and the reaction temperature should be kept below 0^oC. Otherwise the reaction mixture turns orange and a low yield results after chromatography.

¹H (300 MHz, CDCl₃) 7.13-7.26 (m, 4 H, ArH), 6.46 (dd, J = 16.5, 9.8 Hz, 1 H, SC(H)CH2), 6.22 (d, J = 16.5 Hz, 1 H, SCHC(H)H), 5.90 (d, J = 9.8 Hz, 1 H, SCHCH(H)), 4.83 (br s, 1 H, NH), 4.14 (d, J = 6.1 Hz, 2 H, NCH₂), 2.33 (s, 3 H, CH₃), ¹³C (75 MHz, CDCl₃) 137.8 (s), 136.1 (d), 133.5 (s), 129.4 (d), 128.0 (d), 126.7 (t), 46.8 (t), 21.1 (q), m.p = 86-88^oC

Modification of PFP vinyl sulfonate procedure [SP210] or Distler's procedure Distler, H; Angew. Chem., Int. Ed., 1965, 4, 300-311.