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

HRID 1607567

反応式

HRID 1607567 の反応式
[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]

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 22456Lead diacetate trihydrateHCID 852294-Phenylurazole

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-518c97d464134411aa242510dbf40756
出典データセット
uspto-grants-1989_09
特許番号
US04866058

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