3-Pyridinemethanol → HCID 54036716, compound

HRID 258563Notes

Reaction equation

HRID 258563 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C(N(CC)CC)C.[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=1)[C:18](Cl)=[O:19]>C1C=CC=CC=1>[CH3:16][N:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=1)[C:18](=[O:19])[O:8][CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 8471TriethylamineHCID 53891953HCID 53891953, compound

Product 1

HCID 54036716HCID 54036716, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-pyridylcarbinol (2.4 g., 0.0222 mole) in triethylamine (2.24 g., 0.0222 mole) was added dropwise to a solution of N-methyl-(4-methylthiophenyl)carbamoyl chloride in 150 ml. of benzene. The reaction mixture was heated to reflux temperature for about 1 hr. then allowed to stand over night at room temperature. The reaction mixture was washed with water and the benzene layer separated, dried over magnesium sulfate and concentrated in vacuo to give an oil which solidified. The product was recrystallized from methylcyclohexane to give 2.6 g. of solid melting at 100°-102° C. This was a 40.5% yield of 3-pyridylmethyl N-methyl-N-(4-methylthiophenyl)carbamate.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux temperature for about 1 hr
  3. waitto stand over night at room temperature
  4. washThe reaction mixture was washed with water
  5. customthe benzene layer separated
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customThe product was recrystallized from methylcyclohexane
  10. customto give 2.6 g

Sources & evidence

ORD record
ord-dd0db5495bfd479e9b8bf0e124280025
Source dataset
uspto-grants-1977_07
Patent number
US04033972

Reaction notes

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