Ethyl isothiocyanate → 1-[2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-3-ethyl-thiourea-Hydrochloride Salt

HRID 1072524Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072524
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20].[N:21]([CH2:24][CH3:25])=[C:22]=[S:23]>C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:22]([NH:21][CH2:24][CH3:25])=[S:23]

Komponenten

4

Edukt 2

HCID 10966Ethyl isothiocyanateHCID 99225972-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenylamine

Produkt 1

HCID 223869141-[2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenyl]-3-ethyl-thiourea-Hydrochloride SaltAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenylamine (95 mg, example 36) was dissolved in acetonitrile (4 ml) and isothiocyanato-ethane (27 mg) was added to the stirred solution. After standing for 15 h at room temperature the solvent was removed and the residue purified by preparative HPLC. The product containing fractions were combined and the acetonitrile was removed in vaccuo. After addition of potassium carbonate the aqueous phase was extracted with ethyl acetate. The organic layer was separated, dried (magnesium sulphate), filtered and concentrated in vaccuo. The residue was dissolved in water/2N hydrochloric acid and freeze dried to give 36 mg of the title compound.

Aufarbeitung

  1. customthe solvent was removed
  2. customthe residue purified by preparative HPLC
  3. additionThe product containing fractions
  4. customthe acetonitrile was removed in vaccuo
  5. additionAfter addition of potassium carbonate the aqueous phase
  6. extractionwas extracted with ethyl acetate
  7. customThe organic layer was separated
  8. dry with materialdried (magnesium sulphate)
  9. filtrationfiltered
  10. concentrationconcentrated in vaccuo
  11. dissolutionThe residue was dissolved in water/2N hydrochloric acid
  12. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-c4623bc98fec4c489798371ef2e40cab
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911453B2

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