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

HRID 439505노트

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HRID 439505 반응식
[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

참가 물질

4

반응물 2

HCID 24434Potassium NitrateHCID 10733649HCID 10733649, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
25 °C

실험 절차

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): δ12.601 (br, 1H), 12.341 (s, 1H), 7.606 (s, 1H).

후처리

  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

출처 및 근거

ORD 기록
ord-483cb88bb01a4b3a94a89f15a435eb98
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05514680

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