1-Bromopentane → HCID 12557693, compound

HRID 2052386Notes

Reaction equation

HRID 2052386 reaction equation
[O:1]=[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=[C:3]1[NH:9][C:10](=[O:14])[C:11]([OH:13])=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CS(C)=O>[CH2:22]([O:12][C:11](=[O:13])[C:10]([NH:9][C:3]1[C:2](=[O:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:14])[CH2:23][CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 191769N-Troponyloxamic acid

Product 1

HCID 12557693HCID 12557693, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of [(2-oxo-3,5,7-cycloheptatrien-1-yl)amino]oxo-acetic acid (1.54 g, described in Example 30) and potassium carbonate (0.82 g) in dimethylsulfoxide (8 ml) is stirred at room temperature for 15 minutes. A solution of 5-bromopentane (1.52 ml) in dimethylsulfoxide (8 ml) is added and the resulting mixture is stirred at 80° C. for 40 minutes. The mixture is cooled to room temperature and poured over ice. The mixture is stirred for ten minutes and the precipitate is collected by filtration. The precipitate is dissolved in ether, treated with charcoal and crystallized by the addition of hexane to give the title compound, mp 87°-89° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. additionpoured over ice
  3. stirringThe mixture is stirred for ten minutes
  4. filtrationthe precipitate is collected by filtration
  5. dissolutionThe precipitate is dissolved in ether
  6. additiontreated with charcoal
  7. customcrystallized by the addition of hexane

Sources & evidence

ORD record
ord-36acbc0518894c17b04fa4348df6f8d2
Source dataset
uspto-grants-1980_01
Patent number
US04183955

Reaction notes

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