p-Hydroxyaniline mustard → HCID 9956815, compound

Participants

Reaction Steps

Using an analogous procedure to that described in Example 1, 2,3-dimethyl-3-(2,3,5-trimethyl-1,4-benzoquinonyl)butyric acid was reacted with 4-[bis(2-chloroethyl)amino]phenol and the product was purified by column chromatography on silica using a 8.5:1.5 mixture of petroleum ether (b.p. 40 to 60° C.) and ethyl acetate as eluent. There was thus obtained to give 4-[bis(2-chloroethyl)amino]phenyl 2,3-dimethyl-3-(2,3,5-trimethyl-1,4-benzoquinonyl)butyrate as an oil in 20% yield; NMR Spectrum: (CDCl3) 1.25 (d, 3H), 1.45 (s, 3H), 1.50 (s, 3H), 1.95 (s, 3H), 1.97 (s, 3H), 2.21 (s, 3H), 3.60 (t, 4H), 3.67 (t, 4H), 3.85 (q, 1H), 6.61 (d, 2H), 6.82 (d, 2H); Mass Spectrum: (M+Na+) 502, 504 & 506.

Provenance & Evidence