Diethylamine → HCID 117843421, compound

HRID 2209042Notes

Reaction equation

HRID 2209042 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH2:18][CH3:19])[CH:16]=[N:17][C:13]=2[CH:12]=[C:11]([Br:20])[CH:10]=1)C1C=CC=CC=1.B(Br)(Br)Br.C1COCC1.C(NCC)C>C(Cl)Cl.CO>[Br:20][C:11]1[CH:10]=[C:9]([OH:8])[C:14]2[N:15]([CH2:18][CH3:19])[CH:16]=[N:17][C:13]=2[CH:12]=1

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 25134Boron tribromideHCID 117843537HCID 117843537, compound

Product 1

HCID 117843421HCID 117843421, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(benzyloxy)-5-bromo-1-ethyl-1H-benzo[d]imidazole (225 mg, 0.679 mmol) in DCM (8 mL) at 0° C. was added a solution of 1.0 M BBr3 in THF (0.66 mL, 1.5 equiv). After 1 h at 0° C., methanol (1.5 mL), and diethylamine (1.3 mL) were added to the reaction mixture, which was then stirred at rt for 1 h. Reaction mixture was then concentrated and water was added, the solids formed were filtered, washed with water and dried to give the title compound which was used further without purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C9H10BrN2O: 241.0; found: 241.0.

Workup

  1. customReaction mixture
  2. concentrationwas then concentrated
  3. additionwater was added
  4. customthe solids formed
  5. filtrationwere filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-51280da05007496ebe1c8f0797f6568f
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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