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

HRID 361331

反応式

HRID 361331 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-126aee76f0394e8eaa69a8643e72ca91
出典データセット
uspto-grants-1999_02
特許番号
US05866565

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