Methyl Isocyanate → 4-[[(Dimethylamino)methylene]amino]-3-pyridinol methylcarbamate

HRID 361331

반응식

HRID 361331 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+].[CH3:15][N:16]=[C:17]=[O:18]>O1CCCC1>[CH3:15][NH:16][C:17]([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:18]

참가 물질

5

반응물 3

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

생성물 1

HCID 677490744-[[(Dimethylamino)methylene]amino]-3-pyridinol methylcarbamate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a hot suspension of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (7.0 g) in dry tetrahydrofuran (THF) were added sodium hydride (168 mg) and methyl isocyanate (2.6 ml). The reaction mixture was stirred at room temperature overnight, cooled in an ice-methanol bath and filtered. The solid was washed with diethyl ether and distributed between methylene chloride (250 ml) and saturated ammonium chloride (30 ml) and, extracted twice more with methylene chloride (200 ml). The solution was dried (MgSO4) and concentrated and the solid was recrystallized from ethyl acetate and dried under high vacuum and refluxing ethanol to yield 6.18 g of crystals, m.p. 137°-139° C.

후처리

  1. temperaturecooled in an ice-methanol bath
  2. filtrationfiltered
  3. washThe solid was washed with diethyl ether
  4. extractionextracted twice more with methylene chloride (200 ml)
  5. dry with materialThe solution was dried (MgSO4)
  6. concentrationconcentrated
  7. customthe solid was recrystallized from ethyl acetate
  8. customdried under high vacuum
  9. temperaturerefluxing ethanol

출처 및 근거

ORD 기록
ord-126aee76f0394e8eaa69a8643e72ca91
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05866565

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