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【结 构 式】 
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【分子编号】56030 【品名】4-chloro-3-[(3-methyl-2-butenyl)oxy]phenylamine; 4-chloro-3-[(3-methyl-2-butenyl)oxy]aniline 【CA登记号】 |
【 分 子 式 】C11H14ClNO 【 分 子 量 】211.691 【元素组成】C 62.41% H 6.67% Cl 16.75% N 6.62% O 7.56% |
合成路线1
该中间体在本合成路线中的序号：(V)The diazonium salt prepared from 2-amino-5-nitrophenol (I) was subjected to Sandmeyer reaction in the presence of HCl and CuCl to afford the chlorophenol derivative (II). Subsequent alkylation of phenol (II) with prenyl bromide (III) produced ether (IV). Amine (V) was then obtained by reduction of the nitro group of (IV) employing iron powder in the presence of HCl.
| 【1】 Brouwer, W.G.; Osika, E.M.; Pierce, B.J. (Uniroyal Chemical Company, Inc.); Furan- and thiophenecarbothioamide derivs., their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants. EP 0874839; JP 1999504657; US 5696151; WO 9719940 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 33067 | 2-amino-5-nitrophenol | 121-88-0 | C6H6N2O3 | 详情 | 详情 |
| (II) | 56028 | 2-chloro-5-nitrophenol | 619-10-3 | C6H4ClNO3 | 详情 | 详情 |
| (III) | 12989 | 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene | 870-63-3 | C5H9Br | 详情 | 详情 |
| (IV) | 56029 | 1-chloro-2-[(3-methyl-2-butenyl)oxy]-4-nitrobenzene; 2-chloro-5-nitrophenyl 3-methyl-2-butenyl ether | C11H12ClNO3 | 详情 | 详情 | |
| (V) | 56030 | 4-chloro-3-[(3-methyl-2-butenyl)oxy]phenylamine; 4-chloro-3-[(3-methyl-2-butenyl)oxy]aniline | C11H14ClNO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)Chloroacetaldehyde (VII), prepared by acid hydrolysis of the dimethyl ketal (VI), was condensed with ethyl acetoacetate (VIII) to produce ethyl 2-methyl-3-furoate (IX). Basic hydrolysis of ester (IX), followed by chlorination of the resultant carboxylic acid (X) with SOCl2, gave acid chloride (XI). Then, condensation of amine (V) with acid chloride (XI) yielded amide (XII), which was finally converted to the title thioamide by treatment with Lawesson's reagent in hot toluene.
| 【1】 Brouwer, W.G.; Osika, E.M.; Pierce, B.J. (Uniroyal Chemical Company, Inc.); Furan- and thiophenecarbothioamide derivs., their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants. EP 0874839; JP 1999504657; US 5696151; WO 9719940 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 56030 | 4-chloro-3-[(3-methyl-2-butenyl)oxy]phenylamine; 4-chloro-3-[(3-methyl-2-butenyl)oxy]aniline | C11H14ClNO | 详情 | 详情 | |
| (VI) | 56031 | 1-chloro-2,2-dimethoxyethane; 2-Chloro-1,1-dimethoxyethane; Chloroacetaldehyde dimethyl acetal; Dimethyl chloroacetal; Methyl Chloroacetal | 97-97-2 | C4H9ClO2 | 详情 | 详情 |
| (VII) | 47061 | 2-chloroacetaldehyde | 107-20-0 | C2H3ClO | 详情 | 详情 |
| (VIII) | 11819 | ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate | 141-97-9 | C6H10O3 | 详情 | 详情 |
| (IX) | 56032 | Ethyl- 2-methyl-3-furoate | 28921-35-9 | C8H10O3 | 详情 | 详情 |
| (X) | 56033 | 2-Methyl-3-furoic acid | 6947-94-0 | C6H6O3 | 详情 | 详情 |
| (XI) | 56034 | 2-methyl-3-furoyl chloride | 5555-00-0 | C6H5ClO2 | 详情 | 详情 |
| (XII) | 56035 | N-{4-chloro-3-[(3-methyl-2-butenyl)oxy]phenyl}-2-methyl-3-furamide | C17H18ClNO3 | 详情 | 详情 |