Hydrochloric Acid → HCID 86653094, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-5-methylbenzoic acid (2.52 g, 16.7 mmol) and carbon disulfide (2.01 mL, 33.9 mmol) in 45 mL of dry 1,4-dioxane was added NEt3 (5.58 mL, 40.0 mmol) and the mixture were stirred under N2 atmosphere at 5° C. for 18 hours. Iodomethane (1.14 mL, 18.4 mmol) was added dropwise and the mixture was stirred as 5° C. for 1 hour. The reaction was poured into 25 mL of an aqueous solution of HCl (1M) and the mixture was concentrated to half its volume under reduced pressure and extracted three times with 75 mL of EtOAc. The combined organic layers were dried over MgSO4 and concentrated under reduced pressure. The residue was recrystallized from chloroform to give 3 as a yellow solid (3.25 g, 81%). mp: 199° C.

Provenance & Evidence