3-吡啶甲醇 → O-[(Pyridin-3-yl)methyl] (4-cyanophenyl)carbamothioate

HRID 263303

反应方程式

HRID 263303 反应方程式
[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]

参与物

8

反应物 5

HCID 75103-吡啶甲醇HCID 176264-氰基苯基异硫氰酸酯HCID 24758氢化钠HCID 516892碳酸氢钠HCID 2723790硫脲

产物 1

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

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 8071乙二醇二甲醚溶剂2 次

实验过程

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.

后处理

  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

来源与证据

ORD记录
ord-a466d27218384f8aa65905f1c4d56569
来源数据集
uspto-grants-1979_05
专利号
US04156780

关联笔记

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