Triethylamine → N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

HRID 21645

반응식

HRID 21645 반응식
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:5]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 299436N'-tert-butylbenzohydrazide

생성물 1

HCID 15767543N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

A solution of N'-t-butyl-N-benzoylhydrazine (2.0 g) and nicotinoyl chloride hydrochloride in 20 ml of methylene chloride at 23° C. was treated dropwise with triethylamine (4 ml). The reaction mixture was stirred at 23° C. for 0.5 hours. Solids were removed by filtration. The filtrate was diluted with 10N HCl and ether. The layers were separated and the organic layer was washed with 10N HCl. The aqueous layer was neutralized with solid sodium bicarbonate and extracted with ether. The ether extracts were treated with charcoal and then dried with magnesium sulfate. Evaporation of solvents afforded a yellow oil which was chromatographed on silica gel using as eluant a mixture of 10% CH3OH, 40% CH2Cl2, 50% Et2O to afford N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine as a yellow foam: m.p. 60°-63° C.

후처리

  1. customSolids were removed by filtration
  2. additionThe filtrate was diluted with 10N HCl and ether
  3. customThe layers were separated
  4. washthe organic layer was washed with 10N HCl
  5. extractionextracted with ether
  6. additionThe ether extracts were treated with charcoal
  7. dry with materialdried with magnesium sulfate
  8. customEvaporation of solvents
  9. customafforded a yellow oil which
  10. customwas chromatographed on silica gel using as eluant
  11. additiona mixture of 10% CH3OH, 40% CH2Cl2, 50% Et2O

출처 및 근거

ORD 기록
ord-7040c1e3278a4d979435f82d9d30012e
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424333

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