【结 构 式】 |
【分子编号】32697 【品名】2-(benzhydrylsulfanyl)-N-hydroxyacetamide 【CA登记号】63547-44-4 |
【 分 子 式 】C15H15NO2S 【 分 子 量 】273.35564 【元素组成】C 65.91% H 5.53% N 5.12% O 11.71% S 11.73% |
合成路线1
该中间体在本合成路线中的序号:(VI)This compound can be prepared in several different ways: 1) The reaction of benzhydryl bromide (I) with thiourea (II) in refluxing water gives diphenyl - methanethiol (III), which is condensed with chloroacetic acid (A) by means of NaOH in hot water yielding (benzhydrylthio)acetic acid (IV). The esterification of (IV) with ethanol and H2SO4 affords the corresponding ethyl ester (V), which is treated with hydroxylamine hydrochloride and KOH in methanol to give benzhydrylthioacetohydroxamic acid (VI). Finally, this compound is oxidized with H2O2 in acetic acid. 2) Compound (III) can also be obtained by reaction of benzhydrol (VII) with thiourea and aqueous 48% HBr at 100 C. 3) Compound (IV) can be oxidized with H2O2 in water to give benzhydrylsulfinylacetic acid (VIII), which is methylated with dimethyl sulfate and NaHCO3 in water to the corresponding methyl ester (IX). Finally, this compound is treated with hydroxylamine and NaOH in water
【1】 Lafon, L. (Laboratoires L. Lafon); New benzhydrysulphinyl derivatives. DE 2642511; FR 2326181; GB 1520812; JP 52046058; US 4066686 . |
【2】 Mignonac, S.; Guy, A.; De Lamer, V. (Sanofi-Synthelabo); Preparation of polyamine(s), substd. on terminal nitrogen atoms. FR 2714052 . |
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) | 11847 | 2-Chloroacetic acid; Chloroacetic Acid | 79-11-8 | C2H3ClO2 | 详情 | 详情 |
(I) | 12079 | Bromodiphenylmethane; 1-[Bromo(phenyl)methyl]benzene; Benzhydrylbromide | 776-74-9 | C13H11Br | 详情 | 详情 |
(II) | 10180 | Thiourea | 62-56-6 | CH4N2S | 详情 | 详情 |
(III) | 32695 | diphenylmethanethiol; benzhydrylhydrosulfide | C13H12S | 详情 | 详情 | |
(IV) | 11848 | 2-(Benzhydrylsulfanyl)acetic acid | C15H14O2S | 详情 | 详情 | |
(V) | 32696 | ethyl 2-(benzhydrylsulfanyl)acetate | C17H18O2S | 详情 | 详情 | |
(VI) | 32697 | 2-(benzhydrylsulfanyl)-N-hydroxyacetamide | 63547-44-4 | C15H15NO2S | 详情 | 详情 |
(VII) | 11845 | Diphenylmethanol; Benzhydrol | 91-01-0 | C13H12O | 详情 | 详情 |
(VIII) | 11851 | 2-(Benzhydrylsulfinyl)acetic acid | C15H14O3S | 详情 | 详情 | |
(IX) | 11852 | methyl 2-(benzhydrylsulfinyl)acetate | C16H16O3S | 详情 | 详情 |