반응식
CC1OC(S(=O)(=O)N)=C(C(O)=O)C=1.C(C1OC=CC=1)C.N1C=CC=CC=1.S(=O)(=O)=O.[Na].[CH2:32]([C:34]1[O:38][C:37]([S:39]([OH:42])(=[O:41])=O)=[CH:36][CH:35]=1)[CH3:33].P(Cl)(Cl)(Cl)(Cl)Cl.[C:49]([NH2:53])([CH3:52])([CH3:51])[CH3:50]>>[CH2:32]([C:34]1[O:38][C:37]([S:39]([NH:53][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:41])=[O:42])=[CH:36][CH:35]=1)[CH3:33]참가 물질
반응물 7
생성물 1
실험 절차
Analogous to the preparation of the 5-methyl-2-sulfamoyl-furan-3-carboxylic acid (see starting compound of Example 1), 2-ethyl furan was sulfonated with sulfur trioxide-pyridine-complex into the sodium salt of the 5-ethyl-furan-2-sulfonic acid with a yield of 32.5% of theory. After chlorinating it with phosphorus pentachloride and reacting it with tert. butyl amine, 5-ethyl-N-tert. butyl-furan-2-sulfonamide [(m.p. 71°-72° C. from petroleum ether); 1H-NMR (CDCl3): δ=6.95 (d, 1, J=2 Hz, 3-H), 6.15 (d, 1, J=2 Hz, 4-H), 4,7 (s, 1, NH, exchangeable), 2.73 (q, 2, CH2), 1.30 (m, 12, --CH2 --CH3 and C(CH3)3)] was obtained with a yield of 48% of theory. The two subsequent reactions were also performed in analogy to the preparation of the 5-methyl-furan compound: By metalizing with butyl lithium and by carboxylating with carbon dioxide, the 5-ethyl-2-(N-tert. butyl)-sulfamoyl-furan-3-carboxylic acid (m.p. 118°-119° C. from cyclo hexane) was obtained with a yield of 59% of theory, which was heated under dry conditions at 160° C. for 2 hours. 5-Ethyl-2-sulfamoyl-furan-3-carboxylic acid [m.p.: 186° C. (from ethyl acetate), 1 H-NMR ([d6 ]=DMSO); δ=6.6 (s, 1, 4-H), 2.73 (q, 2, CH2), 1.25 (t, 3, CH3) and two exchangeable protons] was obtained with a yield of 87% of theory.
출처 및 근거
- ORD 기록
- ord-6abfc4cb4e344be68c4672923c5a64ab
- 출처 데이터셋
- uspto-grants-1980_11
- 특허 번호
- US04233333
연결된 노트
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