Potassium Nitrate → 6-Bromo-5-nitro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 53786ノート

反応式

HRID 53786 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[NH:8][C:7](=[O:16])[C:6](=[O:17])[NH:5]2.[N+:18]([O-])([O-:20])=[O:19].[K+]>OS(O)(=O)=O>[Br:1][C:2]1[C:3]([N+:18]([O-:20])=[O:19])=[C:4]2[C:9](=[CH:10][C:11]=1[C:12]([F:14])([F:15])[F:13])[NH:8][C:7](=[O:16])[C:6](=[O:17])[NH:5]2

参加物

4

反応物 2

HCID 24434Potassium NitrateHCID 10733649HCID 10733649、化合物

生成物 1

HCID 108319376-Bromo-5-nitro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione収率 74%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

反応条件

温度
25 °C

実験手順

To a solution of 6-bromo-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione (40 mg, 0.13 mmol) in concentrated H2SO4 (0.5 mL) at 25° C. was added KNO3 (16 mg, 0.15 mmol, Baker). The mixture was stirred at 25° C. for 30 h and poured into ice water (2 g). The yellow precipitate was collected by filtration and the solid was dissolved in 1N KOH (10 mL). It was filtered and the filtrate was acidified to pH=5 with 4N HCl (2.5 mL) to give a yellow precipitate. The precipitate was collected and dried in the air at 50° C. for 4 h, affording the title compound (34 mg, 74%) as a yellow powder. Recrystallization from DMSO/H2O gave 18 mg (40%) of the title compound as yellow needles. Mp: 333°-5° C. (dec.); IR (KBr, cm-1): 3428, 3308, 3251, 3207, 1761, 1698, 1537, 600. 1H NMR (DMSO-d6): δ 12.601 (br, 1H), 12.341 (s, 1H), 7.606 (s, 1H).

後処理

  1. filtrationThe yellow precipitate was collected by filtration
  2. dissolutionthe solid was dissolved in 1N KOH (10 mL)
  3. filtrationIt was filtered
  4. customto give a yellow precipitate
  5. customThe precipitate was collected
  6. customdried in the air at 50° C. for 4 h

出典と根拠

ORDレコード
ord-9cd9093dbc5e4d3e816c360f93f9cb1e
出典データセット
uspto-grants-1997_04
特許番号
US05620979

反応ノート

読み込み中…