1,1'-Oxalyldiimidazole → 5-Hydroxy-1,4-dihydroquinoxaline-2,3-dione

HRID 1188728노트

반응식

HRID 1188728 반응식
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[C:10](N1C=CN=C1)(=[O:18])[C:11](N1C=CN=C1)=[O:12]>O1CCCC1>[OH:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[NH:1][C:10](=[O:18])[C:11](=[O:12])[NH:8]2

참가 물질

4

반응물 2

HCID 1004391,1'-OxalyldiimidazoleHCID 5799372,3-Diaminophenol

생성물 1

HCID 451216145-Hydroxy-1,4-dihydroquinoxaline-2,3-dione

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2,3-diaminophenol (50 g) and 1,1′-oxalyldiimidazole (92 g) and tetrahydrofurane (1.2 L) is refluxed 30 minutes. The solvent is removed under reduced pressure and the remaining solid taken into ethyl acetate. The organic phase is washed with 1M aqueous hydrochloric solution, dried over sodium sulphate and concentrated under vacuum. The crude solid obtained is recrystallised from dimethylformamide; yield: 14.8 g; MS: 177.1 (M−1); 1H NMR (DMSO-d6, 300 MHz): δ [ppm] 6.61 (m, 2H); 6.91 (ss, 1H), 10.21 (s (1H); 11.05 (s, 1H); 11.85 (s, 1H).

후처리

  1. customThe solvent is removed under reduced pressure
  2. washThe organic phase is washed with 1M aqueous hydrochloric solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customThe crude solid obtained
  6. customis recrystallised from dimethylformamide

출처 및 근거

ORD 기록
ord-239e0b8a34114f0c8ee65cf28d09e67f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674097B2

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