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

HRID 53715노트

반응식

HRID 53715 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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) δ 11.7 (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.

후처리

  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

출처 및 근거

ORD 기록
ord-4b986a9651e54d9d99b39cfcb7edab99
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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