Acetic Anhydride → 1,2-Diacetyl-4-phenyl-1,2,4-triazolidine-3,5-dione

HRID 1607567

반응식

HRID 1607567 반응식
[C:1]1([N:7]2[C:11](=[O:12])[NH:10][NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.O.O.[C:17]([O-:20])(=O)[CH3:18].[C:21]([O-])(=[O:23])[CH3:22].[Pb+2].C(OC(=O)C)(=O)C>C(Cl)(Cl)Cl>[CH3:22][C:21]([N:10]1[C:11](=[O:12])[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8](=[O:13])[N:9]1[C:17]([CH3:18])=[O:20])=[O:23]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 22456Lead diacetate trihydrateHCID 852294-Phenylurazole

생성물 1

HCID 1514231,2-Diacetyl-4-phenyl-1,2,4-triazolidine-3,5-dione수율 35.1%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a mixture of 5.3 g (30 mmol) of 4-phenyl-1,2,4-triazolidine-3,5-dione and 22.7 g (60 mmol) of lead diacetate trihydrate in 200 ml of chloroform was added dropwise over a 15 minute period 45.9 g (450 mmol) of acetic anhydride. The mixture was stirred at room temperature. After 25 hours the pale yellow solution was washed with three 100 ml portions of water and three 75 ml portions of 10% sodium carbonate. The carbonate washings were acidified with concentrated hydrochloric acid. No precipitate was produced. The chloroform solution was dried (Na2SO4) and evaporated under reduced pressure to give a solid-liquid residue. The residue was filtered and the filtered solid was washed with 25 ml of 95% ethanol to give 2.75 g (35.1%) of the 1,2,4-triazolidine-3,5-dione product as a white solid. An additional quantity of the product precipitated from the ethanol filtrate. This solid was filtered to give an additional 1.20 g (15.3%) of the 1,2,4-triazolidine-3,5-dione product (50.4% total yield). The solids were recrystallized from 95% ethanol to give pure 1,2-dimethylcarbonyl-4-phenyl-1,2,4-triazolidine-3,5-dione: m.p. 169°-170.5° C.; IR (Nujol) 1750, 1732 (shoulder), 1714 (shoulder) Cm-1 (CO); 1H NMR (60 MHz, CDCl3) δ 7.80(s, 5H), 2.55 (s, 6H); Found: C, 55.2; H, 4.45; N, 16.0; C12H 11 N3O4 requires C, 55.2; H, 4.2; N, 16.0.

후처리

  1. washAfter 25 hours the pale yellow solution was washed with three 100 ml portions of water and three 75 ml portions of 10% sodium carbonate
  2. customNo precipitate was produced
  3. dry with materialThe chloroform solution was dried (Na2SO4)
  4. customevaporated under reduced pressure
  5. customto give a solid-liquid residue
  6. filtrationThe residue was filtered
  7. washthe filtered solid was washed with 25 ml of 95% ethanol

출처 및 근거

ORD 기록
ord-518c97d464134411aa242510dbf40756
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04866058

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