(4-Nitrophenyl)acetic acid → HCID 3522175, Verbindung

HRID 2117634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2117634
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(Cl)Cl>C1COCC1.CN(C=O)C>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:21][CH2:20]1

Komponenten

7

Edukt 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 531671-Methylpiperazine

Produkt 1

HCID 3522175HCID 3522175, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Nitrophenylacetic acid (2.00 g, 0.011 mol) was dissolved in anhydrous THF (20 mL) with gradual addition of thionyl chloride (1.03 mL, 0.0143 mol) and a catalytic amount of DMF (2 drops) at room temperature and stirred for 24 h. On completion, the reaction was quenched in situ with N-methylpiperazine (3.85 g, 0.038 mol) added dropwise in a solution of DCM (20 mL) at room temperature and stirred overnight to give a beige suspension. The solvent was removed in vacuo and the residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL). The organic layer was washed twice, dried over sodium sulfate and filtered. Removal of the solvent in vacuo the title compound as an amber oil, which solidified on standing. LCMS:2.5 min; Rt 0.82 (m/z 264, M+H+) 98%

Aufarbeitung

  1. customto give a beige suspension
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL)
  4. washThe organic layer was washed twice
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customRemoval of the solvent in vacuo the title compound as an amber oil, which
  8. custom2.5 min

Quellen und Nachweise

ORD-Eintrag
ord-eb679a379c6d4c13a9db0e8f585e62ad
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07442698B2

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