Triethylamine → HCID 21873648, Verbindung

HRID 1176685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176685
C([O:3][C:4](=O)[C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[C:8]([S:14][CH2:15][C:16](OCC)=[O:17])=[CH:7][C:6]=1[F:21])C.C(OC(=O)C1C=C([N+]([O-])=O)C(F)=CC=1F)C.CCN(CC)CC.SCC(OCC)=O>C(Cl)Cl>[F:21][C:6]1[C:5]([CH:4]=[O:3])=[CH:10][C:9]2[NH:11][C:16](=[O:17])[CH2:15][S:14][C:8]=2[CH:7]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 22330120Ethyl 2,4-difluoro-5-nitrobenzoateHCID 59560604Ethyl 4-[(2-ethoxy-2-oxoethyl)thio]-2-fluoro-5-nitrobenzoate

Produkt 1

HCID 21873648HCID 21873648, VerbindungAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Ethoxycarbonylmethylsulfanyl-2-fluoro-5-nitro-benzoic acid ethyl ester. To a solution of 2,4-difluoro-5-nitro-benzoic acid ethyl ester (7.0 g, 0.030 mol) in CH2Cl2 (125 mL) was added Et3N (5.0 mL, 36 mmol) at 0° C. Following the addition of ethyl 2-mercaptoacetate (3.30 mL, 30.3 mmol), the solution was warmed to RT and stirred for 18 h. The reaction mixture was partitioned between H2O and CH2Cl2 (400 mL). The organic layer was washed with 0.05 M HCl (200 mL), brine (200 mL), dried (MgSO4), filtered and concentrated to provide 9.6 g (96%) of the title compound as a tan solid. MS (ESI): exact mass calculated for C13H14FNO6S, 331.05; m/z not found. 1H NMR (500 MHz, CDCl3): 8.88 (d, J=6.9, 1H), 7.14 (d, J=11.4, 1H), 4.41 (q, J=7.2, 2H), 4.29 (q, J=7.2, 2H), 3.75 (s, 2H), 1.40 (t, J=7.2, 3H), 1.29 (t, J=7.2, 3H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between H2O and CH2Cl2 (400 mL)
  2. washThe organic layer was washed with 0.05 M HCl (200 mL), brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5fc9a45312ac44a8bf2c34043c8063f1
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842810B2

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