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

HRID 263303

Reaction equation

HRID 263303 reaction equation
[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]

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a466d27218384f8aa65905f1c4d56569
Source dataset
uspto-grants-1979_05
Patent number
US04156780

Linked notes

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