Oxalyl chloride → N-[(5-chloro(2-thienyl))sulfonyl]-N'-[4-(5-chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]ethane-1,2-diamide

HRID 562668

反応式

HRID 562668 の反応式
[Cl:1][C:2]1[S:6][C:5]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22](=[O:23])[C:21]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:20]=3[C:19]2=[O:29])=[C:14]([CH3:30])[CH:13]=1.[C:31](Cl)(=[O:35])[C:32](Cl)=[O:33]>>[Cl:1][C:2]1[S:6][C:5]([S:7]([NH:10][C:31](=[O:35])[C:32]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:22](=[O:23])[C:21]4[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:20]=4[C:19]3=[O:29])=[C:14]([CH3:30])[CH:13]=2)=[O:33])(=[O:9])=[O:8])=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 65578Oxalyl chlorideHCID 93991N-(4-Amino-o-tolyl)-4-chlorophthalimideHCID 12413015-Chlorothiophene-2-Sulfonamide

生成物 1

HCID 20800257N-[(5-chloro(2-thienyl))sulfonyl]-N'-[4-(5-chloro-1,3-dioxobenzo [c]azolidin-2-yl)-3-methylphenyl]ethane-1,2-diamide収率 44%

実験手順

A 200 mg (1.0 mmol) of 5-chlorothiophenesulfonamide was slurried in 0.5 mL of oxalyl chloride and refluxed for 6 h. The solvent was removed in vacuo and 36 mg of the resulting solid was dissolved in 240 μl, acetonitrile and treated with 40 mg (0.14 mmol) 2-(4-amino-2-methylphenyl)-5-chlorobenzo[c]azoline-1,3-dione. After stirring for 1 h, the solvent was removed and the residue was purified by RP-HPLC to give 33 mg (44%) of the titled compound. ES-MS (M+H)+=538(2Cl).

後処理

  1. temperaturerefluxed for 6 h
  2. customThe solvent was removed in vacuo and 36 mg of the resulting solid
  3. dissolutionwas dissolved in 240 μl, acetonitrile
  4. customthe solvent was removed
  5. customthe residue was purified by RP-HPLC

出典と根拠

ORDレコード
ord-5b832f5d211849d48ec600fb78bfc494
出典データセット
uspto-grants-2011_11
特許番号
US08067428B2

関連ノート

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