2,4,6-trimethyl-N-propylbenzenesulfonamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaH (60%, 0.70 g, 17 mmol), 65 (3.5 g, 14.5 mmol), and 1,4-dibromobutane (37.6 g, 174 mmol) in DMF (40 mL) were combined and worked up by the method of 43. Excess 1,4-dibromobutane was removed by a Kugelrohr apparatus under high vacuum. Column chromatography (7:1 hexane/EtOAc) produced 5.21 g (95%) of 67 as an oil: NMR δ 0.79 (t, 3 H, J=7), 1.46-1.54 (m, 2 H), 1.64-1.78 (m, 4 H), 2.30 (s, 3 H), 2.60 (s, 6 H), 3.11 (t, 2 H, J=7), 3.21 (t, 2 H, J=7), 3.31 (t, 2 H, J=7), 6.93 (s, 2 H). Anal. (C16H26BrNO2S) C, H, N. Excess 1,4-dibromobutane was removed by a Kugelrohr apparatus under high vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: NaH (60%, 0.34 g, 8.4 mmol), 65 (1.7 g, 7.0 mmol), and 1,3-dibromopropane (17.0 g, 84 mmol) in DMF (30 mL) were combined and worked up by the method of 43. Column chromatography (6:1 hexane/EtOAc) produced 1.82 g (80%) of 66 as an oil: NMR δ 0.79 (s, 3 H), 1.48-1.56 (m, 2 H), 2.04-2.10 (m, 2 H), 2.30 (s, 3 H), 2.60 (s, 6 H), 3.09-3.14 (m, 2 H), 3.29-3.36 (m, 4 H). Anal. (C15H24BrNO2S) C, H, N.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mesitylenesulfonyl chloride (12.0 g, 55 mmol) and propylamine (2.96 g, 50 mmol) in CH2Cl2 (60 mL) and 1 N NaOH (60 mL) were combined and worked up by the method of 31. Column chromatography (3:1 hexane/EtOAc) afforded 8.44 g (85%) of 65 as a crystalline solid: mp 53-54° C.; NMR δ 0.86 (t, 3 H, J=7), 1.44-1.51 (m, 2 H), 2.30 (s, 3 H), 2.64 (s, 6 H), 2.86 (q, 2 H), 4.40 (br t, 1 H), 6.96 (s, 2 H). Anal. (C12H19NO2S) C, H, N.