2-Nitrobenzyl alcohol → (2-Nitrophenyl)methyl N-cyclohexylcarbamate

HRID 442599Notes

Reaction equation

HRID 442599 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][OH:7])([O-:3])=[O:2].[CH:12]1([N:18]=[C:19]=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[CH:12]1([NH:18][C:19](=[O:20])[O:7][CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 119232-Nitrobenzyl alcoholHCID 18502Cyclohexyl isocyanate2×

Product 1

HCID 21910133(2-Nitrophenyl)methyl N-cyclohexylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10 mL toluene, 3.1 g 2-nitrobenzyl alcohol, and 2.5 g cyclohexylisocyanate were introduced into a 100-mL three-neck flask and heated under reflux for 1 hour under nitrogen. After cooling, an additional 0.5 g cyclohexylisocyanate was added and the reaction was stirred for 1 hour at ambient temperature. The reaction solution was then washed several times with water and the resulting toluene solution was dried over sodium sulfate. The sodium sulfate was thereafter filtered off and the solvent was eliminated from the filtrate on a rotary evaporator. The resulting solid was recrystallized from toluene to yield ortho-nitrobenzyl cyclohexylcarbamate as light-yellow, needle-like crystals. mp=101°-102° C. Identification by the proton NMR spectrum.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour under nitrogen
  3. temperatureAfter cooling
  4. washThe reaction solution was then washed several times with water
  5. dry with materialthe resulting toluene solution was dried over sodium sulfate
  6. filtrationThe sodium sulfate was thereafter filtered off
  7. customthe solvent was eliminated from the filtrate on a rotary evaporator
  8. customThe resulting solid was recrystallized from toluene

Sources & evidence

ORD record
ord-a617c26638054dba8697dfdaaf9add5b
Source dataset
uspto-grants-1999_04
Patent number
US05891529

Reaction notes

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