Ethyl Acetate → N-(6-mercaptoisoquinolin-1-yl)benzamide

HRID 1366745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366745
[OH-].[Na+].[C:3]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([S:22]C(=O)N(C)C)=[CH:19][CH:20]=2)[CH:15]=[CH:14][N:13]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>O.O.CO.C1COCC1.CCCCCCC>[SH:22][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:12]([NH:11][C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[N:13][CH:14]=[CH:15]2

Komponenten

8

Edukt 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86612976dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester

Produkt 1

HCID 136378996N-(6-mercaptoisoquinolin-1-yl)benzamideAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittelHCID 447138Water dimerLösungsmittel

Versuchsvorschrift

A solution of NaOH (92 mg) in water H2O (1 ml) was added to a solution of dimethylthiocarbamic acid S-(1-benzoylaminoisoquinolin-6-yl)ester (70 mg) in MeOH (1 ml) and THF (1 ml). The mixture was stirred for 1 h at ambient temperature then for a further 1 h at 56° C. The organics were removed in vacuo then the mixture was diluted with water and acidified with dilute hydrochloric acid (pH˜3.5). The mixture was extracted with ethyl acetate (X3), dried (sodium sulphate) and concentrated in vacuo to give a residue. Flash chromatography of the residue (eluent: 1-5% ethyl acetate in heptane) gave N-(6-mercaptoisoquinolin-1-yl)-benzamide (30 mg).

Aufarbeitung

  1. waitfor a further 1 h at 56° C
  2. customThe organics were removed in vacuo
  3. additionthe mixture was diluted with water
  4. extractionThe mixture was extracted with ethyl acetate (X3)
  5. dry with materialdried (sodium sulphate)
  6. concentrationconcentrated in vacuo
  7. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-1f4c81053dbd453ebe5b477757186187
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893088B2

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