Diethyl Oxalate → HCID 650260, 화합물

HRID 53711

반응식

HRID 53711 반응식
[C:1]([O:8]CC)(=O)[C:2]([O:4]CC)=O.[Cl:11][C:12]1[C:13]([NH2:20])=[C:14]([NH2:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1>>[Cl:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]2[C:13]=1[NH:20][C:2](=[O:4])[C:1](=[O:8])[NH:19]2

참가 물질

3

반응물 2

HCID 7268Diethyl OxalateHCID 42768353,5-Dichlorobenzene-1,2-diamine

생성물 1

HCID 650260HCID 650260, 화합물

실험 절차

The title compound (Leeson, P. D. et al., J. Med. Chem 34: 1243 (1991)) was prepared using an adaptation of the method of Cheeseman. (Cheeseman, G. W. H. J. Chem. Soc. 1171 (1962)). A mixture of diethyl oxalate (4.12 g, 28.2 mmol) and 3,5-dichloro-1,2-diaminobenzene (500 mg, 2.82 mmol) was heated to reflux under N2 for 6 h. The reaction was allowed to cool to room temperature and the pale yellow shiny solid collected by vacuum filtration and rinsed with EtOH (20 mL) and air dried to give 286 mg (44%). mp 326°-328° C. (dec) Lit 337°-340° C.). 1H NMR (d6 -DMSO) δ 7.05 (d, 1H, J=1.8, H-8), 7.32 (d, 1H, J=1.8, H-6), 11.5 (br s, 1H, NH), 12.1 (br s, 1H, NH). EIMS m/e 234 (M+4, 12), 232 (M+2, 67), 230 (M+, bp), 204 (52), 202 (77), 141 (19), 142 (59) EIHRMS calc. for C8H4Cl2N2O: 229.9650, found 229.9646.

후처리

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 6 h
  3. filtrationthe pale yellow shiny solid collected by vacuum filtration
  4. washrinsed with EtOH (20 mL) and air
  5. customdried
  6. customto give 286 mg (44%)
  7. custommp 326°-328° C. (dec) Lit 337°-340° C.

출처 및 근거

ORD 기록
ord-ec8bc8f85f27423cb34524fc9ed7152e
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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