Dimethylformamide → HCID 86601512, compound

Participants

Reaction Conditions

Reaction Steps

6-Bromohexanoic acid (1.0 g, 5.1 mmol) and Sodium Methanethiosulfonate (750 mg, 5.6 mmol, 1.1 eq prepared according to Kenyon and Bruice, Methods Enzymol. (1977), 47, 407-430) were dissolved in 10 mL of dimethylformamide (DMF), warmed to 55° C. and stirred overnight. The reaction mixture was concentrated to syrup and taken up in CHCl3 (30 mL), washed with H2O (5×50 mL) and the organic phase was dried with anhydrous sodium sulfate. Concentration by rotary evaporation and elimination of residual solvent with high vacuum yielded 890 mg (78%) of white solid comprising 6-carboxyhexyl methanethiosulfonate. 1H NMR: δ 3.31 (s, 3H, CH3SO2S), 3.16 (t, J=7.5 Hz, 2H, SCH2), 2.37 (t, J=7.2 Hz, 2H, CH2COOH), 1.79 (m, 2H, CH2CH2S), 1.67 (m, 2H, CH2CH2COOH), 1.48 (m, 2H).

Provenance & Evidence