3-Pyridinemethanol → Carbamic acid, (4-(methylthio)phenyl)-, 3-pyridinylmethyl ester

HRID 1579408Notes

Reaction equation

HRID 1579408 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[CH3:9][S:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>C1N2CCN(CC2)C1.C1C=CC=CC=1>[CH3:9][S:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][C:18](=[O:19])[O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 75103-PyridinemethanolHCID 27333164-(Methylthio)phenyl isocyanate

Product 1

HCID 40069Carbamic acid, (4-(methylthio)phenyl)-, 3-pyridinylmethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 4.4 g. (0.04 mole) of 3-pyridylcarbinol in 50 ml. of benzene containing 0.1 g. of Dabco catalyst was added, dropwise, a solution of 6.6 g. (0.04 mole) of p-methylthiophenyl isocyanate (New Haven Chemicals) in 50 ml. of benzene. During the addition a white solid separated and the temperature rose from 23°C. to 34°C. The mixture was stirred at ambient temperature for 16 hrs. and the product was filtered off. After oven-drying in vacuo there was obtained 10.4 g. melting at 133° -135°C. This is a 95% yield of 3-pyridylmethyl N-(4'-methylthiophenyl)-carbamate.

Workup

  1. additionDuring the addition a white solid
  2. customseparated
  3. customrose from 23°C. to 34°C
  4. filtrationand the product was filtered off
  5. customAfter oven-drying in vacuo
  6. customthere was obtained 10.4 g

Sources & evidence

ORD record
ord-11eef2577a1542ab9cf86b047a8e622d
Source dataset
uspto-grants-1976_01
Patent number
US03931202

Reaction notes

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