3-Pyridinemethanol → Carbamic acid, [4-(cyanomethyl)phenyl]-, 3-pyridinylmethyl ester

HRID 839268Notes

Reaction equation

HRID 839268 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)#[N:2].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][OH:20])[CH:14]=1>C1C=CC=CC=1>[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][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:6][CH:5]=1)#[N:2]

Participants

4

Reactant 2

HCID 75103-PyridinemethanolHCID 46018354-Isocyanatobenzyl cyanide

Product 1

HCID 20324109Carbamic acid, [4-(cyanomethyl)phenyl]-, 3-pyridinylmethyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of p-cyanomethylphenyl isocyanate (3.75 g., 0.0237 mole) in 100 ml. of benzene was added 3-pyridyl carbinol (2.59 g., 0.0237 mole). An exothermic reaction occurred and a precipitate formed. The reaction mixture was heated to reflux then allowed to stand at ambient temperatures for 3 hrs. The solid was filtered off and dried to give 5.8 g. melting at 157°-161.5° C. The product is a 92% yield of 3-pyridylmethyl N-(4-cyanomethylphenyl)carbamate. Recrystallization from methanol gave a solid melting at 162°-163.5° C.

Workup

  1. customAn exothermic reaction
  2. customa precipitate formed
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux
  5. filtrationThe solid was filtered off
  6. customdried
  7. customto give 5.8 g

Sources & evidence

ORD record
ord-69dd4d2c23d641929cdaccc9e767efa3
Source dataset
uspto-grants-1978_06
Patent number
US04094875

Reaction notes

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