Boron tribromide → HCID 135666746, compound

HRID 1583764Notes

Reaction equation

HRID 1583764 reaction equation
C[O:2][C:3]1[C:11]2[C:7](=[N:8][C:9](=[O:12])[N:10]=2)[C:6]([CH2:13][CH2:14][N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])=[CH:5][CH:4]=1.B(Br)(Br)[Br:23]>C(Cl)Cl>[BrH:23].[OH:2][C:3]1[C:11]2[C:7](=[N:8][C:9](=[O:12])[N:10]=2)[C:6]([CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH3:18])[CH2:19][CH2:20][CH3:21])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 20258371HCID 20258371, compound

Product 1

HCID 135666746HCID 135666746, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.83 g (0.00629 m) of 4-methoxy-7-[2-(N,N-di-n-propylamino)ethyl]-1,3-benzimidazol-2-one in 100 ml of methylene chloride was cooled to -30° while 17.5 ml of 1M boron tribromide in methylene chloride was added dropwise. After standing at room temperature for 4 hours, the mixture yielded an oil which solidified. The residue was triturated with methanol, then recrystallized from isopropanol to give 1.94 g (86%) of 4-hydroxy-7-[2-(N,N-di-n-propylamino)ethyl]-1,3-benzimidazol-2-one hydrobromide; 240°-242°.

Workup

  1. additionwas added dropwise
  2. customthe mixture yielded an oil which
  3. customThe residue was triturated with methanol
  4. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-d31a48f58f5348f7ab4ef1d933627dd7
Source dataset
uspto-grants-1985_11
Patent number
US04554287

Reaction notes

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