Diethyl Oxalate → HCID 650260、化合物

HRID 54299

反応式

HRID 54299 の反応式
[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

参加物

3

反応物 2

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

生成物 1

HCID 650260HCID 650260、化合物

実験手順

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) δ7.05 (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 C8H4Cl2N2O2 229.9650, found 229.9646.

後処理

  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.

出典と根拠

ORDレコード
ord-f542b0f0d597415083dc46f85a3cb260
出典データセット
uspto-grants-1997_04
特許番号
US05622952

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