3-[(phenylsulfonyl)methyl]aniline hydrochloride3 -[(phenylsulfonyl)甲基]苯胺盐酸盐.pdfVIP

Molbank 2006 /molbank/molbank2006/m502.ht Molbank 2006, M502 /molbank/ 3-[(Phenylsulfonyl)methyl]aniline hydrochloride Daniel G. Grohmann and Bruce A. Hathaway* Department of Chemistry, MS 6400, One University Plaza, Southeast Missouri State University, Cape Girardeau, MO, USA, Tel. 001 573-651-2370, e-mail: bahathaway@ *Author to whom correspondence should be addressed Received: 6 July 2006 / Accepted: 1 August 2006 / Published: 1 September 2006 Keywords: nitro, amine, reduction. In the course of our work to prepare inhibitors of the enzyme dihydrofolate reductase, we desired to prepare sulfone analogues of some previously reported sulfides [1, 2]. The previously reported nitrosulfone [3] was not able to be reduced to the amine by using catalytic hydrogenation with a palladium on carbon catalyst, with tin and hydrochloric acid [4], or with iron and acetic acid in ethanol [5]. Therefore, the nitrosulfone, 1, was converted into the acetamide, 2, using iron in acetic acid [5]. The acetamide, 2, was hydrolyzed to the desired aniline, 3, using concentrated hydrochloric acid and ethanol. Unfortunately for us, the aniline was not able to be converted into the desired triazine by the reported procedure [2]. In round bottom flask 1-nitro-3-[(phenylsulfonyl)methyl]benzene, 1 (2.453 g, 8.85 mmoles), iron filings (2.019 g, 36.2 mmoles), and 25 mL of concentrated acetic acid were combined and refluxed overnight. After allowing the flask to cool, 200 mL of water and 100 mL of dichloromethane were added to the mixture. The unreacted iron was then removed by vacuum filtration. The aqueous and organic layers