Diethyl Ether → HCID 10686834, compound

Participants

Reaction Conditions

Reaction Steps

To 0.5 g (1.68 mmoles) of the nitrile of Example 52 in 10 mL dry C6H6 was added 1.1 mL (3.3 mmoles) of a 3 M solution CH3MgI in ether and the mixture was stirred at 25° C. for 2 h and at reflux for 1 h. The reaction was quenched with water and 10% HCl and stirred for 20 min before 1 M NaOH was added until the solution was alkaline and the mixture was extracted with 100 mL EtOAc. The organic layer was washed with water, brine, dried and stripped in vacuo. The residue was chromatographed on silica gel using 20% EtOAc/hexanes to give 370 mg product (70% yield); mp 125-126° C. Elemental analysis for C17H21N3OS: Theory C, 64.73; H, 6.71; N, 13.32; S, 10.16. Found C, 64.53; H, 6.73; N, 13.08; S, 10.19.

Provenance & Evidence