Ethylenediamine → 2,5-Dichloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole

HRID 23402Notes

Reaction equation

HRID 23402 reaction equation
[CH2:1](N)[CH2:2][NH2:3].Cl.C(O[C:9](=[NH:26])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[C:13]([S:21]([CH3:24])(=[O:23])=[O:22])=[C:12]1[Cl:25])C>C(O)C.C(Cl)(Cl)Cl>[Cl:25][C:12]1[N:11]([CH2:10][C:9]2[NH:26][CH2:1][CH2:2][N:3]=2)[C:19]2[C:14]([C:13]=1[S:21]([CH3:24])(=[O:22])=[O:23])=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 695462252-(2,5-Dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochloride

Product 1

HCID 225739652,5-Dichloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indoleYield 99.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Procedure

To a solution of ethylene diamine(0.065 g, 1.092 mmole) in ethanol:chloroform (30 ml, 1:1) at 0° C. under a nitrogen atmosphere was added 2-(2,5-dichloro-3-methanesulfonyl-indol-1-yl)-acetimidic acid ethyl ester hydrochloride (0.351 g, 0.91 mmole) dissolved in chloroform (5 ml). The reaction mixture was stirred at room temperature for 2 h and then evaporated to dryness. The residue was purified by column chromatography (silica gel) eluting the product with 7:93 methanol:methylene chloride with 0.1% ammonium hydroxide added. The resulting product, pure 2,5-dichloro-1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-3-methanesulfonyl-1H-indole weighed 0.314 g (99.7% yield).

Workup

  1. customevaporated to dryness
  2. customThe residue was purified by column chromatography (silica gel)
  3. washeluting the product with 7:93 methanol
  4. additionmethylene chloride with 0.1% ammonium hydroxide added

Sources & evidence

ORD record
ord-d80187d6692f45baa8867e56c5126b7b
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Reaction notes

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