Tetrahydrofuran → HCID 21192539、化合物

HRID 1068018ノート

反応式

HRID 1068018 の反応式
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([I:21])=[CH:15][CH:14]=3)=[S:9])=[CH:4][CH:3]=1.[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1.N(C(OCC)=O)=NC(OCC)=O>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([I:21])[CH:17]=3)[N:12]([CH3:24])[CH:11]=2)=[S:9])=[CH:22][CH:23]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回HCID 178516665HCID 178516665、化合物

生成物 1

HCID 21192539HCID 21192539、化合物収率 31.5%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a suspension of N-(4-chlorobenzyl)-4-hydroxy-6-iodo-3-quinolinecarbothioamide (0.20 g) from Preparation No. 43 and triphenylphosphine (0.15 g) in freshly distilled tetrahydrofuran (5 mL) is added MeOH (0.027 mL) followed by diethyl azodicarboxylate. After an initial exotherm, the reaction is stirred at room temperature for 3 h. To drive the reaction to completion, additional triphenylphosphine (0.030 g), methanol (0.010 mL), and diethyl azodicarboxylate (0.020 mL) are added. The reaction is stirred at room temperature overnight. The reaction is concentrated in vacuo. The residue is dissolved in CH2Cl2 and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1 L), 1% MeOH:CH2Cl2 (1 L)) affords N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarbothioamide (0.065 g) as a yellow solid.

後処理

  1. customfrom Preparation No
  2. additionare added
  3. stirringThe reaction is stirred at room temperature overnight
  4. concentrationThe reaction is concentrated in vacuo
  5. dissolutionThe residue is dissolved in CH2Cl2
  6. customPurification by chromatography (eluent CH2Cl2 (1 L), 1% MeOH:CH2Cl2 (1 L))

出典と根拠

ORDレコード
ord-79fd63f7095e48fe92342b925126ba3f
出典データセット
uspto-grants-2001_06
特許番号
US06248739B1

反応ノート

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