Ammonia → HCID 18379857, compound

HRID 429583Notes

Reaction equation

HRID 429583 reaction equation
[Br: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.CO.CCOC(C)=O>CC(O)=O>[Br:17][C:5]1[C:6]2[NH:10][CH:9]=[N:8][C:7]=2[C:2]([Br:1])=[CH:3][C:4]=1[NH:11][C:12]1[NH:13][CH2:14][CH2:15][N:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 10468857HCID 10468857, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 18379857HCID 18379857, compoundYield 136.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 7-bromo-5-(2-imidazolin-2-ylamino)benzimidazole (0.6 g, 2.1 mmol) in 10 ml of AcOH was added Br2 (0.057 ml, 1.1 mmol) in a portion. The resulting reaction mixture was stirred for 1 h at 25° C. Concentration of reaction mixture in vacuo yields a brown oil which was subjected to column chromatography (30% NH3 sat'd MeOH/EtOAc) to provides 0.28 g (1.5 mmol, 71%) of the desired product. The product obtained was recrystallized from MeOH to afford 0.22 g (56%) of the product as a light brown solid: mp 320≠321° C.; Anal. Calc. for C10H9N5Br2 requires C, 33.45; H, 2.53; N, 19.51. Found: C, 33.93; H, 4.05; N, 19.01.

Workup

  1. customThe resulting reaction mixture
  2. customConcentration of reaction mixture in vacuo
  3. customyields a brown oil which

Sources & evidence

ORD record
ord-592b15cfff724281a3e1e3d1192a53f3
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

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