3-Pyridinemethanol → HCID 20387958, compound

HRID 1579407Notes

Reaction equation

HRID 1579407 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.[F:9][C:10]([F:21])([F:20])[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>[F:9][C:10]([F:20])([F:21])[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 737684-(Trifluoromethyl)phenyl isocyanate

Product 1

HCID 20387958HCID 20387958, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9237DabcoCatalystHCID 241BenzeneSolvent2×

Procedure

To a solution of 2.5 g. (0.023 mole) of 3-pyridylcarbinol in 50 ml. of benzene containing 0.1 g. of Dabco catalyst (1,4-diazabicyclo [2,2,2] octane) was added, dropwise, a solution of 43 g. (0.023 mole) of p-trifluoromethyl-phenyl isocyanate in 50 ml. of benzene. A temperature rise from 23° to 35° was noted during the addition, and a white precipitate formed. After stirring for 1 hr., the mixture was filtered, and the solid product was air-dried. There was obtained 6.3 g. (93% of theory) of product; melting point 173° - 175° C. (decomposed). This is a 93% yield of 3-pyridylmethyl N-(4'-trifluoromethylphenyl)-carbamate.

Workup

  1. additionA temperature rise from 23° to 35° was noted during the addition
  2. customa white precipitate formed
  3. filtration, the mixture was filtered
  4. customthe solid product was air-dried
  5. customThere was obtained 6.3 g

Sources & evidence

ORD record
ord-1f2e43b3a0564321ac3b243ed5abd4f4
Source dataset
uspto-grants-1976_01
Patent number
US03931202

Reaction notes

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