2-Furancarboxylic acid → HCID 11694247, compound

HRID 1432134Notes

Reaction equation

HRID 1432134 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.S(Cl)(Cl)=O.[CH3:13][N:14]1[CH:19]2[CH2:20][CH2:21][CH:15]1[CH2:16][NH:17][CH2:18]2.[OH-].[Na+]>COCCOC.C1(C)C=CC=CC=1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:17]1[CH2:18][CH:19]2[N:14]([CH3:13])[CH:15]([CH2:21][CH2:20]2)[CH2:16]1)=[O:8]

Participants

7

Reactant 4

HCID 69192-Furancarboxylic acidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 4229248-Methyl-3,8-diazabicyclo[3.2.1]octane

Product 1

HCID 11694247HCID 11694247, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-furoic acid (1.33 g, 11.9 mmol) and thionyl chloride (20 ml) was stirred at reflux for 2 hours. The mixture was evaporated and co-evaporated with toluene, 8-methyl-3,8-diaza-bicyclo[3.2.1]octane (1.5 g, 11.9 mmol) and 1,2-dimethoxyethane (40 ml) was added and was stirred at room temperature for 15 hours. Aqueous sodium hydroxide (50 ml, 1M) was added and the mixture was extracted twice with dichloromethane (2×40 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as a solid. Mp. 106° C. Yield 1.41 g (54%).

Workup

  1. temperatureat reflux for 2 hours
  2. customThe mixture was evaporated
  3. additionwas added
  4. stirringwas stirred at room temperature for 15 hours
  5. extractionthe mixture was extracted twice with dichloromethane (2×40 ml)

Sources & evidence

ORD record
ord-b63adedaa04c4c68a4c7caefed794f52
Source dataset
uspto-grants-2009_11
Patent number
US07612074B2

Reaction notes

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