반응식
[C:1]([O:4][CH2:5][CH2:6]C(O)=O)(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:17])C=CC=CC=1.C([N:29]([CH2:32]C)CC)C.[NH2:34][CH2:35][C:36]1[O:40][C:39]([C:41]2[N:42]=[C:43]([N:46]=[C:47]([NH2:49])[NH2:48])[S:44][CH:45]=2)=[CH:38][CH:37]=1>C1C=CC=CC=1.CO.O1CCCC1>[C:1]([O:4][CH2:5][CH2:6][NH:29][C:32](=[O:17])[NH:34][CH2:35][C:36]1[O:40][C:39]([C:41]2[N:42]=[C:43]([N:46]=[C:47]([NH2:49])[NH2:48])[S:44][CH:45]=2)=[CH:38][CH:37]=1)(=[O:3])[CH3:2]참가 물질
반응물 4
생성물 1
시약·촉매·용매 3
실험 절차
A mixture of 3-acetoxypropionic acid (2.5 g), diphenylphosphorylazide (4.3 ml) and triethylamine (2.6 ml) in dry benzene (50 ml) was stirred for an hour at 75° to 80° C. To the mixture was added to a mixture of 4-(5-aminomethylfuran-2-yl)-2-(diaminomethyleneamino)thiazole (3.0 g) in a solution of tetrahydrofuran (45 ml) and methanol (45 ml) at ambient temperature, and the mixture was stirred for 2.5 hours at the same temperature. Evaporation of a solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and methanol (9:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was recrystallized from a mixture of methanol, dioxane and isopropyl ether to give 4-[5-{3-(2-acetoxyethyl)ureido}methylfuran-2-yl]-2-(diaminomethyleneamino)thiazole (1.82 g).
후처리
- stirringthe mixture was stirred for 2.5 hours at the same temperature
- customEvaporation of a solvent
- customgave a residue, which
- customwas purified by column chromatography on silica gel eluting with a mixture of ethyl acetate and methanol (9:1, V/V)
- additionThe eluted fractions containing the desired product
- customwere collected
- customevaporated in vacuo
- customThe residue was recrystallized from a mixture of methanol, dioxane and isopropyl ether
출처 및 근거
- ORD 기록
- ord-1e35ba9396e84701a89f6491da912058
- 출처 데이터셋
- uspto-grants-1994_05
- 특허 번호
- US05308857
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