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

HRID 1188728ノート

反応式

HRID 1188728 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-239e0b8a34114f0c8ee65cf28d09e67f
出典データセット
uspto-grants-2014_03
特許番号
US08674097B2

反応ノート

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