3-Pyridinemethanol → O-[(Pyridin-3-yl)methyl] (4-cyanophenyl)carbamothioate

HRID 263303

反応式

HRID 263303 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[H-].[Na+].[C:11]([C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[S:21])=[CH:15][CH:14]=1)#[N:12].C(=O)(O)[O-].[Na+].NC(N)=S>O.C(COC)OC>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([NH:19][C:20](=[S:21])[O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:17][CH:18]=1)#[N:12]

参加物

8

反応物 5

HCID 75103-PyridinemethanolHCID 17626Benzonitrile, 4-isothiocyanato-HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 2723790Thiourea

生成物 1

HCID 12790266O-[(Pyridin-3-yl)methyl] (4-cyanophenyl)carbamothioate収率 43.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

To a solution of 3-pyridylcarbinol (2.18g., 0.02 mole) in 50 ml. of glyme there is added sodium hydride (0.87g. of a 57% oil dispersion, 0.02 mole). The solution is allowed to stand 2 hrs. and then p-cyanophenyl isothiocyanate (3.2g., 0.02 mole) in 50 ml. of glyme is added dropwise. The reaction mixture is stirred at room temperature for 18 hrs. It is then saturated with sodium bicarbonate and poured into an excess of water. The resulting suspension is filtered to give a solid residue which is recrystallized from toluene to give 2.3g. of solid melting at 153°-154° C., with decomposition. The thiourea structure is confirmed by infra-red spectroscopy. The product is obtained in a 43.5% yield.

後処理

  1. filtrationThe resulting suspension is filtered
  2. customto give a solid residue which
  3. customis recrystallized from toluene
  4. customto give 2.3g
  5. customThe product is obtained in a 43.5% yield

出典と根拠

ORDレコード
ord-a466d27218384f8aa65905f1c4d56569
出典データセット
uspto-grants-1979_05
特許番号
US04156780

関連ノート

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