4-Nitrobenzyl alcohol → HCID 19896605, compound

HRID 1196867Notes

Reaction equation

HRID 1196867 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[C:11](C1NC=CN=1)(C1NC=CN=1)=[O:12].[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30][OH:31])=[CH:28][CH:27]=1)([O-:25])=[O:24]>CC#N.N1C=CN=C1.[Na]>[C:11](=[O:12])([O:31][CH2:30][C:29]1[CH:28]=[CH:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:33][CH:32]=1)[O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 692754-Nitrobenzyl alcoholHCID 592968[4-(Methylsulfanyl)phenyl]methanolHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 19896605HCID 19896605, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 57373095Imidazole sodiumCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of p-(methylthio)benzyl alcohol (1.0 g, 6.48 mmol), carbonyl diimidazole (1.16 g, 7.13 mmol) and sodium imidazole (0.010 g) in CH3CN (25 mL) was stirred at 20° C. for 30 min, followed by addition of p-nitrobenzyl alcohol (1.09 g, 7.13 mmol). Stirring was continued for an additional 24 h and then the reaction mixture was evaporated to dryness. The crude carbonate was purified by silica gel chromatography (eluted with CH2Cl2) to afford 2.13 g (98.6%) of the title compound as a white solid, melting at 84°-86° C.

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customThe crude carbonate was purified by silica gel chromatography (eluted with CH2Cl2)

Sources & evidence

ORD record
ord-5dd053a4e506493a81c5c1ca4eebf485
Source dataset
uspto-grants-1992_05
Patent number
US05116833

Reaction notes

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