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

HRID 568303

반응식

HRID 568303 반응식
[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

참가 물질

4

반응물 2

HCID 2906CyclopentylamineHCID 14099147Phenyl pyridazin-4-ylcarbamate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-72751b774d7d4e85889ba395ee64ee29
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04728355

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