3-Pyridinemethanol → Mieshuan

HRID 1579406Notes

Reaction equation

HRID 1579406 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1>C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:12])[O:20][CH2:19][C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 66012Benzene, 1-isocyanato-4-nitro-

Product 1

HCID 40068MieshuanYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

p-Nitrophenylisocyanate (0.1 mole) was added to a solution of 3-pyridylcarbinol (0.1 mole) in 300 ml. of benzene. An exothermic reaction took place and a yellow solid formed. The suspension was heated to reflux and then stirred for 2 hours. The suspension was then cooled and filtered, affording 27 g. of a crude product melting at 230°-231° C. (decomposed). This is a 99% yield of 3-pyridylmethyl N-(4'-nitrophenyl)-carbamate. The product was purified by recrystallization from 2-methoxyethanol (methyl Cellosolve).

Workup

  1. customAn exothermic reaction
  2. customa yellow solid formed
  3. temperatureThe suspension was heated
  4. temperatureto reflux
  5. temperatureThe suspension was then cooled
  6. filtrationfiltered
  7. customaffording 27 g

Sources & evidence

ORD record
ord-15c7a3cc735741d98d34f34b723b332c
Source dataset
uspto-grants-1976_01
Patent number
US03931202

Reaction notes

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