Benzenethiol, 2-amino-4-chloro-, hydrochloride (1:1) → HCID 22148788, compound

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Reaction Steps

By a modification of the procedure of D. L. Boger (J. Org. Chem. 43:2296-2297 (1978)) a solution of P2O5/MeSO3H (Aldrich, 7.5 g, 1:10, w:w) was treated with 2-amino-4-chlorobenzenethiol hydrochloride (Example 6, 1.96 g, 10.0 mmol) and (2,6-dichloro-4-nitro-phenyl)-acetic acid (2.50 g, 10.0 mmol). The resulting mixture was stirred at room temperature for 1 hour, then heated at 90° C. overnight (15 hours). After cooled to room temperature, the reaction mixture was poured to ice and the resulting mixture was extracted 3× with EtOAc (50 mL). The organic layers were combined and washed twice with a brine solution (100 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (CH2Cl2) to yield 3.7 g (99%) of compound 8 as a pale yellow solid. 1H NMR (CDCl3) δ 8.28 (s, 2H), 7.98 (d, J=1.9 Hz, 1H), 7.76 (d, J=8.5 Hz, 1H), 7.38 (dd, J=8.5, 1.9 Hz, 1H), 4.87 (s, 2H). MS (M+H) 373.

Provenance & Evidence