Triethylamine → HCID 376100, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of the above diol (IX) (1.90 g, 5.43 mmol) and Et3N (1.90 mL, 14 mmol) in dry THF (60 mL) was treated dropwise at 0° C. with methanesulfonyl chloride (0.89 mL, 11 mmol). After a further 15 min, the solution was diluted with EtOAc, washed well with water, and worked up to give the crude dimesylate (Id: X=OSO2Me, R=SO2NH2). This was immediately dissolved in DMF (50 mL) containing LiCl (20 g), and the mixture stirred at 130° C. for 15 min before solvent was removed under reduced pressure. The residue was partitioned between EtOAc and water, and the organic layer was worked up and chromatographed on silica gel. Elution with EtOAc gave 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzenesulfonamide (18) (Id: X=Cl, R=SO2NH2) (1.47 g, 64%), mp 153°-154° C. (EtOAc/petroleum ether). 1H NMR ((CD3)2CO) δ 8.54. (S, 1H, H-3), 7.99 (br, 2H, SO2NH2), 7.91 (S, 1H, H-6), 3.84 (t, J=5.6 Hz, 4H, CH2Cl), 3.67 (t, J=5.6 Hz, 4H, CH2N). 13C NMR ((CD3)2CO) δ 146.13 (C-5), 140.64 (C-1), 138.86, 136.93 (C-2,4), 124.95, 121.77 (C-3,6), 52.47 (CH2N), 41.62 (CH2Cl). Anal. (C10H12Cl2N4O6S) C,H,N,S.

Provenance & Evidence