Water → HCID 178418245, 화합물

HRID 1607

반응식

HRID 1607 반응식
[H-].[Na+].[O:3]=[C:4]1[NH:9][C:8]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH2:16][C:7]=2[N:6]2[CH:17]=[C:18]([C:20]([O:22]CC)=[O:21])[N:19]=[C:5]12.[N:25](OCCC(C)C)=[O:26].O>CS(C)=O.C(O)(=O)C>[OH:26][N:25]=[C:16]1[C:7]2[N:6]3[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[N:19]=[C:5]3[C:4](=[O:3])[NH:9][C:8]=2[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]1=2

참가 물질

7

반응물 4

HCID 962WaterHCID 8053Isoamyl NitriteHCID 24758Sodium hydrideHCID 19691063ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate

생성물 1

HCID 178418245HCID 178418245, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매

실험 절차

0.34 g of sodium hydride is added to 1 g of ethyl 4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylate in solution in 20 ml of anhydrous dimethyl sulphoxide, while the temperature of the reaction mixture is maintained below 20° C. 0.44 ml of isoamyl nitrite is then added and stirring is continued for 18 hours at the same temperature. The reaction mixture is then poured into iced water and the solution is acidified with 15 ml of acetic acid. The precipitate formed is filtered off, washed with water, with acetone and then with methanol and finally dried under reduced pressure (1 mm Hg; 0.13 kPa) to produce 0.25 g of 10-hydroxyimino-4,5-dihydro-4-oxo-imidazo[1,2-a]indeno[1,2-e]pyrazine-2-carboxylic acid in the form of a brown powder whose melting point is higher than 260° C. (1H spectrum in DMSO, T=300K, δ in ppm (200 MHz), mixture of the syn and anti isomers: Major isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.62 (1H, s, CH arom.), 7.82 (1H, d, J=7 Hz, CH arom.), 8.00 (1H, s, CH arom.), 8.20 (1H, d, J=7 Hz, CH arom.), 12.7 (1H, s, NH), 13.0 (1H, s, OH), Minor isomer: between 7.30 and 7.50 (2H, m, CH arom.), 7.51 (1H, s, CH arom.), 7.70 (1H, d, J=7 Hz, CH arom.), 7.88 (1H, d, J=7 Hz, CH arom.), 8.58 (1H, s, CH arom.), 12.7 (1H, s, NH), 13.2 (1H, s, OH)).

후처리

  1. temperatureis maintained below 20° C
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with water, with acetone
  5. dry with materialwith methanol and finally dried under reduced pressure (1 mm Hg; 0.13 kPa)

출처 및 근거

ORD 기록
ord-71deb639e501406b8994cac9a143516e
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726175

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