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【结 构 式】

【分子编号】33366

【品名】N-(tert-butyl)(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methanesulfonamide

【CA登记号】

【 分 子 式 】C13H16N2O4S

【 分 子 量 】296.34712

【元素组成】C 52.69% H 5.44% N 9.45% O 21.6% S 10.82%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

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
Extended Information