Lithium iodide → 1-(benzofurazan-5-yl)-2-{N-[2-(benzofurazan-5-oxy)ethyl]-N-methylamino}ethane, hydrochloride

HRID 1195681Notes

Reaction equation

HRID 1195681 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]2[C:8]([CH:12]=1)=[N:9][O:10][N:11]=2.Br.[CH3:14][NH:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]2[C:23]([CH:27]=1)=[N:24][O:25][N:26]=2.C(=O)(O)[O-].[Na+].[I-].[Li+].CO.C(Cl)(Cl)[Cl:38]>C(O)C.CCCCCC>[ClH:38].[N:11]1[O:10][N:9]=[C:8]2[CH:12]=[C:4]([CH2:3][CH2:2][N:15]([CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[C:23]([CH:27]=3)=[N:24][O:25][N:26]=4)[CH3:14])[CH:5]=[CH:6][C:7]=12

Participants

8

Reactant 5

HCID 66321Lithium iodideHCID 516892Sodium BicarbonateHCID 117758995-(2-Bromoethyl)benzofurazanHCID 21584188Chloroform methanolHCID 679164435-(2-Methylaminoethoxy)benzofurazan hydrobromide

Product 1

HCID 679163811-(benzofurazan-5-yl)-2-{N-[2-(benzofurazan-5-oxy)ethyl]-N-methylamino}ethane, hydrochlorideYield 23%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

A suspension of 5-(2-bromoethyl)benzofurazan (245 mg, 1.08 mmol), 5-(2-methylaminoethoxy)benzofurazan hydrobromide (100 mg, 0.36 mmol), sodium bicarbonate (134 mg, 1.6 mmol) and lithium iodide (2 mg) in ethanol (7.0 ml) was heated at reflux temperature overnight. The reaction mixture was concentrated under reduced pressure and saturated sodium bicarbonate solution added. Extraction with methylene chloride, drying and solvent evaporation gave an oil. Flash chromatography (silica gel, methanol-chloroform, 1%), salt formation and trituration with hexane gave 1-(benzofurazan-5-yl)-2-{N-[2-(benzofurazan-5-oxy)ethyl]-N-methylamino}ethane, hydrochloride (31 mg, 23%); mp 214°-216° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature overnight
  3. concentrationThe reaction mixture was concentrated under reduced pressure and saturated sodium bicarbonate solution
  4. additionadded
  5. extractionExtraction with methylene chloride
  6. customdrying
  7. customsolvent evaporation
  8. customgave an oil

Sources & evidence

ORD record
ord-3071e88727ca4d66b19656a01f71595f
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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