3-Pyridinemethanol → (Pyridin-3-yl)methyl (4-sulfanylphenyl)carbamate

HRID 1659111Notes

Reaction equation

HRID 1659111 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][OH:18])[CH:12]=1>C1C=CC=CC=1>[SH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:10])[O:18][CH2:17][C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 190755954-Isocyanatobenzene-1-thiol

Product 1

HCID 21527247(Pyridin-3-yl)methyl (4-sulfanylphenyl)carbamateYield 78%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Mercaptophenyl isocyanate (0.9g., 0.00595 mole) was added to a solution of 3-pyridyl carbinol (0.65g., 0.00595 mole) in 50 ml. of benzene and the reaction mixture was allowed to stand over the weekend. It was then heated to reflux to assure completion of the reaction and then cooled to give a white solid. This was isolated as 1.2g. and was a 78% yield of 3-pyridylmethyl N-(4'-mercaptophenyl)carbamate.

Workup

  1. temperatureIt was then heated
  2. temperatureto reflux
  3. customcompletion of the reaction
  4. temperaturecooled
  5. customto give a white solid
  6. customThis was isolated as 1.2g

Sources & evidence

ORD record
ord-4207c6ba287347beaf6154113f8adf6a
Source dataset
uspto-grants-1976_06
Patent number
US03966947

Reaction notes

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