3-Bromobenzyl bromide → 1-[(3-bromophenyl)methyl]-1H-imidazole-5-propanol

HRID 973949

Reaktionsgleichung

Reaktionsgleichung von HRID 973949
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[CH:3]=1.CN(C)C([N:14]1[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][O:22][Si](C)(C)C)[N:16]=[CH:15]1)=O>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:16]2[C:17]([CH2:19][CH2:20][CH2:21][OH:22])=[CH:18][N:14]=[CH:15]2)[CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 699793-Bromobenzyl bromideHCID 112772221-Dimethylcarbamoyl-4-(3-trimethylsilyloxypropyl)imidazole

Produkt 1

HCID 150356691-[(3-bromophenyl)methyl]-1H-imidazole-5-propanolAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 250 parts of 1-bromo-3-bromomethylbenzene, 168.5 parts of N,N-dimethyl-4-[3-[(trimethylsilyl)oxy]propyl]-1H-imidazole-1-carboxamide and 869 parts of acetonitrile was refluxed for 18 hours. After cooling to 0° C., ammonia was bubbled through the reaction mixture for 5 min. The solvent was evaporated and the residue was stirred for 1 hour in 1700 ml of hydrochloric acid 1N. The mixture was extracted with ethyl acetate. The aqueous layer was basified with Na2CO3 (sat.) and reextracted with ethyl acetate (5×450 parts). The combined extracts were washed with water, dried, filtered and evaporated, yielding 210 parts (100%) of 1-[(3-bromophenyl)methyl]-1H-imidazole-5-propanol (interm. 1).

Aufarbeitung

  1. customammonia was bubbled through the reaction mixture for 5 min
  2. customThe solvent was evaporated
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-94c0f80aa981442d9037134b965a85be
Quelldatensatz
uspto-grants-1991_11
Patentnummer
US05066656

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