Ammonium Hydroxide → 1-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

HRID 1747414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1747414
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24].[NH4+:25].[OH-]>C1COCC1>[NH2:25][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24]

Komponenten

4

Edukt 2

HCID 14923Ammonium HydroxideHCID 594972451-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Produkt 1

HCID 594974891-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-oneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (55 mg, 0.14 mmol) is dissolved in THF (1.5 mL) and NH4OH (1.5 mL, 27% aqueous) is added into it at room temperature. The mixture is then stirred for 16 hr at 65° C. and another one week at room temperature. Then the solvents are removed under vacuum and the residue is washed with THF. The solid formed is filtered and rinsed with more THF to give 28 mg (61%) of 1-(2-Amino-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one.

Aufarbeitung

  1. customThen the solvents are removed under vacuum
  2. washthe residue is washed with THF
  3. customThe solid formed
  4. filtrationis filtered
  5. washrinsed with more THF

Quellen und Nachweise

ORD-Eintrag
ord-b940f4ea734643d0a893b7f9a06a66c5
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150556B2

Notizen zur Reaktion

Wird geladen…