Triethylamine → HCID 57962249, Verbindung

HRID 541831Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 541831
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.C(N(CC)CC)C.[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37](O)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>C(Cl)Cl.O1CCCC1>[N+:27]([C:30]1[CH:31]=[C:32]([CH2:36][C:37]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH:5]=[CH:6][CH:7]=2)=[O:38])[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 158763-Nitrophenylacetic acidHCID 24386Thionyl ChlorideHCID 12877220tert-butyl N-(3-aminophenyl)carbamate

Produkt 1

HCID 57962249HCID 57962249, VerbindungAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

tert-Butyl (3-aminophenyl)carbamate (1.0 g, 4.8 mmol) was dissolved in methylene chloride (4 mL) and then thionyl chloride (2.0 mL, 27 mmol) was added. The mixture was heated at 80° C. for 1 h. The solvent was removed under vacuum. Tetrahydrofuran (20 mL), triethylamine (2.3 mL, 17 mmol) and (3-nitrophenyl)acetic acid (0.87 g, 4.8 mmol) were then added and the mixture was stirred at rt for 1 h. The solvent was removed under vacuum and then EtOAc and water were added. The aqueous phase was extracted again with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a white powder (1.70 g, 95%). LCMS for C19H21N3O5 (M-tBu+H)+: m/z=316.0.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customThe solvent was removed under vacuum
  3. additionEtOAc and water were added
  4. extractionThe aqueous phase was extracted again with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e2541d32f1104380a9192b61b1a40acb
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871753B2

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