Ethylenediamine → HCID 18789725, compound

HRID 1106712Notes

Reaction equation

HRID 1106712 reaction equation
[ClH:1].C(O[C:5](=[NH:19])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=1)C.[CH2:20](N)[CH2:21][NH2:22]>CO>[ClH:1].[NH:22]1[CH2:21][CH2:20][N:19]=[C:5]1[CH2:6][O:7][C:8]1[CH:9]=[C:10]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 69351950HCID 69351950, compound

Product 1

HCID 18789725HCID 18789725, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(3-Methanesulfonylaminophenoxy)-acetimidic acid ethyl ester hydrochloride (0.8 g) was suspended in 12 ml of absolute methanol (MeOH) and treated with 0.16 g of ethylene diamine. After 8 hours at room temperature the solvent was evaporated. The residue was purified by silica gel chromatography eluting with methanol:dichloromethane:ammonium hydroxide (16:84:0.1). Conversion to the hydrochloride salt by addition of 1.0M hydrogen chloride in ether gave 0.16 g of N-[3-(4,5-dihydro-1H-imidazol-2-ylmethoxy) phenyl] methanesulfonamide hydrochloride, mp 183-187° C.

Workup

  1. customAfter 8 hours at room temperature the solvent was evaporated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with methanol:dichloromethane:ammonium hydroxide (16:84:0.1)
  4. additionConversion to the hydrochloride salt by addition of 1.0M hydrogen chloride in ether

Sources & evidence

ORD record
ord-c7cf42a84feb4fda8c78f85cee4b7c7b
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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