Potassium Carbonate → Fentrazamide

HRID 2379386Notes

Reaction equation

HRID 2379386 reaction equation
[CH:1]1[CH:6]=[C:5]([N:7]2[NH:12][N:11]=[N:10][C:8]2=[O:9])[C:4]([Cl:13])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH:20]1([N:26]([CH2:30][CH3:31])[C:27](Cl)=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(#N)C>[CH3:31][CH2:30][N:26]([C:27]([N:10]1[N:11]=[N:12][N:7]([C:5]2[C:4]([Cl:13])=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:8]1=[O:9])=[O:28])[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11332952Cyclohexylethylcarbamoyl chlorideHCID 178518972HCID 178518972, compound

Product 1

HCID 3081363FentrazamideYield 84.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-chlorophenyl)-5(4H)-tetrazolinone (2 g) and potassium carbonate (1.68 g) were suspended in acetonitrile (30 ml), followed by fifteen minutes heating under refluxing. After cooling, N-cyclohexyl-N-ethylcarbamoyl chloride (2.31 g) was added to the reaction mixture, followed by a further five-hour heating under refluxing. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure, and the resulting residue was subjected to flush column chromatography (hexane:ethylacetate=5:2), to obtain the desired 1-(2-chlorophenyl)-4-(N-cyclohexyl-N-ethylcarbamoyl)- 5(4H)-tetrazolinone (3.02 g) having a m.p. in the range of from 77.5° to 79.5° C.

Workup

  1. waitfollowed by fifteen minutes
  2. temperatureheating
  3. temperatureunder refluxing
  4. temperatureAfter cooling
  5. waitfollowed by a further five-hour
  6. temperatureheating
  7. temperatureunder refluxing
  8. filtrationThe resulting mixture was filtered
  9. customthe filtrate was evaporated under reduced pressure
  10. customto flush column chromatography (hexane:ethylacetate=5:2)

Sources & evidence

ORD record
ord-902967fcd3174e2cb0ecfc5a42206fea
Source dataset
uspto-grants-1994_11
Patent number
US05362704

Reaction notes

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