Cyclopentylamine → N-Cyclopentyl-N′-4-pyridazinylurea

HRID 568303

Reaction equation

HRID 568303 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:16])OC2C=CC=CC=2)=[CH:3][N:2]=1.[CH:17]1([NH2:22])[CH2:21][CH2:20][CH2:19][CH2:18]1>O1CCCC1>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]([NH:22][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:16])=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 14099147Phenyl pyridazin-4-ylcarbamate

Product 1

HCID 14099149N-Cyclopentyl-N′-4-pyridazinylureaYield 10.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of 2.0 grams (0.009 mole) of phenyl N-(4-pyridazinyl)carbamate and 1.0 ml (0.010 mole) of cyclopentylamine in tetrahydrofuran is heated under reflux for 18 hours. The reaction mixture is filtered and the filtrate concentrated under reduced pressure to a residue. The residue is purified by column chromatography on silica gel. Elution is accomplished with 10% methanol in methylene chloride. The appropriate fractions are combined and concentrated under reduced pressure to yield 0.2 gram of N-(4-pyridazinyl)-N'-cyclopentylurea. This material is combined with the identical product from a previous reaction to yield 0.5 gram; m.p. 192°-195° C., dec. The nmr spectrum is consistent with the proposed structure. The reaction is repeated several times.

Workup

  1. temperatureunder reflux for 18 hours
  2. filtrationThe reaction mixture is filtered
  3. concentrationthe filtrate concentrated under reduced pressure to a residue
  4. customThe residue is purified by column chromatography on silica gel
  5. washElution
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-72751b774d7d4e85889ba395ee64ee29
Source dataset
uspto-grants-1988_03
Patent number
US04728355

Linked notes

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