Ethyl isocyanate → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol ethylcarbamate

HRID 361332

반응식

HRID 361332 반응식
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].[H-].[Na+].[CH2:15]([N:17]=[C:18]=[O:19])[CH3:16]>O1CCCC1>[CH2:15]([NH:17][C:18]([O:12][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:6]=1[N:5]=[CH:4][N:2]([CH3:1])[CH3:3])=[O:19])[CH3:16]

참가 물질

5

반응물 3

HCID 8022Ethyl isocyanateHCID 24758Sodium hydrideHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

생성물 1

HCID 677490814-[[(Dimethylamino)methylene]amino]-3-pyridinol ethylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a warm solution of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (7.12 g) in dry tetrahydrofuran (150 mL) were added sodium hydride (173 mg) and ethyl isocyanate (3.59 mL). The reaction mixture was stirred at room temperature overnight, cooled in an ice bath and filtered, and the solid was washed with diethyl ether. The solid was distributed between methylene chloride (250 mL) and saturated ammonium chloride (30 mL) and extracted twice more with methylene chloride (100 mL). The solution was dried (MgSO4) and concentrated, and the solid was recrystallized from ethyl acetate to yield 5.7 g of needles, m.p. 138° C. (dec.).

후처리

  1. temperaturecooled in an ice bath
  2. filtrationfiltered
  3. washthe solid was washed with diethyl ether
  4. extractionextracted twice more with methylene chloride (100 mL)
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe solid was recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-eebf09d61fdd47db921fe997da173ffc
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866565

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