Diethyl Oxalate → 5,6,7,8-Tetrachloro-1,4-dihydro-2,3-quinoxalinedione

HRID 439436ノート

反応式

HRID 439436 の反応式
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[NH2:11][C:12]1[C:17]([Cl:18])=[C:16]([Cl:19])[C:15]([Cl:20])=[C:14]([Cl:21])[C:13]=1[NH2:22]>>[Cl:18][C:17]1[C:16]([Cl:19])=[C:15]([Cl:20])[C:14]([Cl:21])=[C:13]2[C:12]=1[NH:11][C:2](=[O:4])[C:1](=[O:8])[NH:22]2

参加物

3

反応物 2

HCID 7268Diethyl OxalateHCID 2817911,2-Diamino-3,4,5,6-tetrachlorobenzene

生成物 1

HCID 3337015,6,7,8-Tetrachloro-1,4-dihydro-2,3-quinoxalinedione

実験手順

5,6,7,8-Tetrachloro-1,4-dihydro-2,3-quinoxalinedione was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (2.97 g, 20.0 mmol) and 1,2-diamino-3,4,5,6-tetrachlorobenzene (500 mg, 2.03 mmol) was heated to reflux under N2 for 6 h. The reaction was allowed to cool to room temperature and the orange solid collected by vacuum filtration and rinsed with cold EtOH (10 mL) and air dried. This solid was recrystallized from abs. ethanol to give 97.0 mg (16%) of an orange solid mp 326°-328° C. (dec). (Lit., >360°). FT-IR: 3198, 3135 cm-1 (N--H), 1750, 1623 cm-1 (C=O). 1H NMR δ (d6 -DMSO) δ11.7 (br s, 2H, N--H) EIMS m/z 306 (M+8, 1.7), 304 (M+6, 11.5), 302 (M+4, 47.4), 300 (M+2, 93.9), 288 (M+, 76.7), 274 (50.0), 272 (bp), 270 (79.0), 209 (61.0), 207 (64.0). EIHRMS calc. for C8H2Cl4N2O2 297.8870, found 297.8864.

後処理

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 6 h
  3. filtrationthe orange solid collected by vacuum filtration
  4. washrinsed with cold EtOH (10 mL) and air
  5. customdried
  6. customThis solid was recrystallized from abs

出典と根拠

ORDレコード
ord-f4787b80584742f2a6bb76299892a948
出典データセット
uspto-grants-1996_05
特許番号
US05514680

反応ノート

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