Chloroform → 4,7-dimethyl-3H-benzimidazol-5-amine

HRID 429584Notes

Reaction equation

HRID 429584 reaction equation
Br[C:2]1[C:10]2[NH:9]C=N[C:6]=2[C:5](Br)=[CH:4][C:3]=1[NH2:12].C[Sn](C)(C)C.[CH:18](Cl)(Cl)Cl.C[N:23]([CH:25]=O)[CH3:24]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][C:2]1[C:3]2[NH:12][CH:25]=[N:23][C:24]=2[C:5]([CH3:4])=[CH:6][C:10]=1[NH2:9]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 11661TetramethyltinHCID 183798914,7-Dibromo-5-aminobenzimidazole

Product 1

HCID 183798614,7-dimethyl-3H-benzimidazol-5-amine

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A solution of 4,7-dibromo-5-aminobenzimidazole (1.5 g, 5.1 mmol) in 10 ml of DMF was transferred into pressure bottle under Ar2. To the solution was added tetramethyltin (3.6 ml, 20 mmol) and bis(triphenylphosphine)palladium(II) chloride (200 mg). The resulting reaction mixture was stirred at 140° C. for 24 h and concentrated in vacuo, yielding a dark oil which was subjected to column chromatography (40% EtOAC/CHCl3) to yield 0.34 g (1.5 mmol, 29%) of the desired product as well as 0.75 g of 4,7-dimethyl-5-aminobenzimidazole.

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. customyielding a dark oil which

Sources & evidence

ORD record
ord-a67ec018bafc4a2bb81694a337c611a1
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Reaction notes

Loading…