Sodium chloroacetate → 5-Chloro-2-(chloromethyl)-1-[3-(methylsulfonyl)propyl]-1H-benzimidazole

HRID 1500843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1500843
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:10](=O)OC(C)(C)C.[Cl:24][CH2:25]C([O-])=O.[Na+]>Cl>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[N:9]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:10]([CH2:25][Cl:24])=[N:1][C:2]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 23665759Sodium chloroacetateHCID 89923659Tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate

Produkt 1

HCID 618081805-Chloro-2-(chloromethyl)-1-[3-(methylsulfonyl)propyl]-1H-benzimidazoleAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of tert-butyl 2-amino-4-chlorophenyl(3-(methylsulfonyl)propyl)carbamate (320 mg, 0.92 mmol) and sodium chloroacetate (130 mg, 1.1 mmol) in 4 N HCl was heated to 100° C. After overnight stirring, the reaction solution was cooled to RT and concentrated. The residue was diluted with DCM (100 mL) and washed with sat. NaHCO3 (50 mL). The organic layer was dried and concentrated under vacuum. The residue was purified by prep-TLC (DCM/EtOAc=3:1) to give 5-chloro-2-(chloromethyl)-1-(3-(methylsulfonyl)propyl)-1H-benzo[d]imidazole (130 mg, yield: 44%) as pale solid. MS obsd. (ESI+) [(M+H)+]: 321.0.

Aufarbeitung

  1. temperaturethe reaction solution was cooled to RT
  2. concentrationconcentrated
  3. additionThe residue was diluted with DCM (100 mL)
  4. washwashed with sat. NaHCO3 (50 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by prep-TLC (DCM/EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f546e6ba87dd442a95836d5b46375dab
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206191B2

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