Ethanethiol → HCID 21462366, compound

Participants

Reaction Steps

To a solution of boron trifluoride etherate (1.57 gm, 10.8 mmol) and ethanethiol (2.31 mL, 1.94 gm, 32.32 mmol) under N2, at room temperature was added dropwise a solution of the compound of Step F, Example 3, (500.0 mg) in CH2Cl2 (1 mL). The resultant clear solution was stirred at room temperature for 48 hours and the reaction was scrubbed with a bleach/50% NaOH/H2O-20%. 30 mL of water was added dropwise at room temperature followed by CH2Cl2 (30 mL). The aqueous layer was separated and basified to pH 10 using 50% NaOH. Additional 30 mL of CH2Cl2 was added and the organic layer was separated, dried (MgSO4) and evaporated to dryness to give the title compound of Step G as a white solid (200 mg), 57%; m.p. 196°-198° C.; IR (nujol, cm-1): 1676.0 (C=O), 3357.7 and 3301.7 (NH); 1H NMR δ: 0.08-0.09 (m,1H), 0.71-0.77 (m,1H), 1.41-1.43 (m,1H), 2.01-2.08 (m,1H), 2.11-2.17 (broad s, 1H), 2.31-2.32 (m,1H), 3.02 (s,2H), 3.72 (s,1H), 4.61 (s,2H), 4.75-4.81 (dd,2H), 6.79-6.81 (d,1H), 8.44-8.46 (d,1H), 9.85 (broad s,1H).

Provenance & Evidence