【结 构 式】 |
【分子编号】33368 【品名】methyl [(tert-butylamino)sulfonyl]methylcarbamodithioate 【CA登记号】 |
【 分 子 式 】C7H16N2O2S3 【 分 子 量 】256.41432 【元素组成】C 32.79% H 6.29% N 10.93% O 12.48% S 37.52% |
合成路线1
该中间体在本合成路线中的序号:(VII)The reaction of aminomethansulfonic acid (I) with phthalic anhydride (II) by means of potassium acetate in refluxing acetic acid gives phthalimidomethansulfonic acid (III), which by reaction with PCl5 in refluxing benzene is converted into its acyl chloride (IV). The condensation of (IV) with tert-butylamine (A) in CHCl3 affords N-tert-butylphthalimidomethansulfonamide (V), which by reaction with hydrazine hydrate in refluxing ethanol yields 2-aminomethan-N-tert-butylsulfonamide (VI). The reaction of (VI) with CS2 and MeI by means of triethylamine in ethanol gives N-tert-butylsulfamoylmethyldithiocarbamic acid methyl ester (VII), which is cyclized with NaN3 in hot water to afford 1-(N-tert-butylsulfamoylmethyl)tetrazol-5-thiol (VIII). The hydrolysis of (VIII) with trifluoroacetic acid yields compound 1-sulfamoylmethyltetrazol-5-thiol (IX).
【1】 Berges, D.A.; 7-Acyl-3-(sulfonic acid and sulfamoyl substituted tetrazolyl thiomethyl)cephalosporins.. DE 2611270; FR 2304343; US 4048311 . |
【2】 Castaner, J.; Serradell, M.N.; Thorpe, P.; Blancafort, P.; Cefonicid sodium. Drugs Fut 1979, 4, 9, 634. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(A) | 17895 | 2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine | 75-64-9 | C4H11N | 详情 | 详情 |
(I) | 33363 | aminomethanesulfonic acid | 13881-91-9 | CH5NO3S | 详情 | 详情 |
(II) | 11900 | 2-Benzofuran-1,3-dione;1,2-Benzenedicarboxylic Anhydride;1,2-BENZENE DICARBOXYLIC ACID ANHYDRIDE;1,2-BENZENEDICARBONIC ACID, ANHYDRIDE;1,3-DIOXOPHTHALAN;1,3-ISOBENZOFURANDIONE;o-phthalic anhydride; Phthalic anhydride | 85-44-9 | C8H4O3 | 详情 | 详情 |
(III) | 33364 | (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methanesulfonic acid | C9H7NO5S | 详情 | 详情 | |
(IV) | 33365 | (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methanesulfonyl chloride | C9H6ClNO4S | 详情 | 详情 | |
(V) | 33366 | N-(tert-butyl)(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methanesulfonamide | C13H16N2O4S | 详情 | 详情 | |
(VI) | 33367 | amino-N-(tert-butyl)methanesulfonamide | C5H14N2O2S | 详情 | 详情 | |
(VII) | 33368 | methyl [(tert-butylamino)sulfonyl]methylcarbamodithioate | C7H16N2O2S3 | 详情 | 详情 | |
(VIII) | 33369 | N-(tert-butyl)(5-sulfanyl-1H-1,2,3,4-tetraazol-1-yl)methanesulfonamide | C6H13N5O2S2 | 详情 | 详情 | |
(IX) | 33370 | (5-sulfanyl-1H-1,2,3,4-tetraazol-1-yl)methanesulfonic acid | C2H4N4O3S2 | 详情 | 详情 |