3-Aminopyridine → (E)-N-cinnamyl-N'-(3-pyridyl) urea

HRID 477003노트

반응식

HRID 477003 반응식
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].N[C:14]1C=NC=C[CH:19]=1.C(N)/C=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH2:12]([NH:8][C:1]([NH:3][C:7]1[CH:6]=[N:5][CH:4]=[CH:14][CH:19]=1)=[O:2])/[CH:11]=[CH:22]/[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

5

반응물 3

HCID 100093-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 6008559cinnamylamine

생성물 1

HCID 14834216(E)-N-cinnamyl-N'-(3-pyridyl) urea수율 233.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 50 ml of a tetrahydrofuran solution containing 16.2 g of carbonyldiimidazole, a solution of 9.4 g of 3-aminopyridine dissolved in 50 ml of tetrahydrofuran was added dropwise under ice-cooling over 5 minutes. After stirring under ice-cooling for 30 minutes and at room temperature for 1 hour, the mixture was again ice-cooled, and 1.33 g of (E)-cinnamylamine was added, followed by stirring at room temperature for 18 hours. After distilling the solvent off, the residue was dissolved in ethyl acetate, washed with water and dried, followed by distillation of the solvent. The residue was purified by silica gel column chromatography (solvent: chloroform-methanol=20:1) to give 5.9 g of (E)-N-cinnamyl-N'-(3-pyridyl) urea as colorless caramel.

후처리

  1. additionwas added dropwise under ice-
  2. temperaturecooling over 5 minutes
  3. temperaturecooled
  4. stirringby stirring at room temperature for 18 hours
  5. distillationAfter distilling the solvent off, the residue
  6. dissolutionwas dissolved in ethyl acetate
  7. washwashed with water
  8. customdried
  9. distillationfollowed by distillation of the solvent
  10. customThe residue was purified by silica gel column chromatography (solvent: chloroform-methanol=20:1)

출처 및 근거

ORD 기록
ord-97c44f7008054c8591a1d3f809c41caa
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04886817

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