Ammonia → HCID 18379816, compound

HRID 2304749Notes

Reaction equation

HRID 2304749 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][NH:10][C:6]=2[CH:5]=[C:4]([NH:11][C:12]2[NH:13][CH2:14][CH2:15][N:16]=2)[CH:3]=1.[Br:17]Br.N>CC(O)=O>[Br:17][C:5]1[C:6]2[NH:10][CH:9]=[N:8][C:7]=2[C:2]([Cl:1])=[CH:3][C:4]=1[NH:11][C:12]1[NH:13][CH2:14][CH2:15][N:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24408BromineHCID 18379878HCID 18379878, compound

Product 1

HCID 18379816HCID 18379816, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-chloro-5-(2-imidazolin-2-ylamino)benzimidazole (0.61 g, 2.6 mmol) in 10 ml of AcOH was added 0.3 ml of Br2. Resulting reaction mixture was stirred for 12 h at 25° C. and concentrated in vacuo, yielding an oil, which was subjected to column chromatography (NH3 sat'd 30% MeOH/EtoAc) to yield 0.23 g (0.85 mmol, 33%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from MeOH to afford 0.12 g (12%) of the product as a light yellow solid: mp 244-246° C.; Anal. Calc. for C10H9N5BrCl.1.0C4H4O4.0.5H2O requires C, 37.77; H, 3.17; N, 18.35. Found: C, 37.75; H, 3.08; N, 18.21.

Workup

  1. customResulting
  2. customreaction mixture
  3. concentrationconcentrated in vacuo
  4. customyielding an oil, which

Sources & evidence

ORD record
ord-766bdbaef971473bad7e73ac3136cea9
Source dataset
uspto-grants-2002_08
Patent number
US06436982B1

Reaction notes

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