Tetrahydrofuran → HCID 21192539, 화합물

HRID 1068018노트

반응식

HRID 1068018 반응식
[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

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 178516665HCID 178516665, 화합물

생성물 1

HCID 21192539HCID 21192539, 화합물수율 31.5%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

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.

후처리

  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))

출처 및 근거

ORD 기록
ord-79fd63f7095e48fe92342b925126ba3f
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248739B1

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