Pyridine → HCID 59862492, compound

HRID 1695512Notes

Reaction equation

HRID 1695512 reaction equation
N1C=CC=CC=1.[N+:7]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[CH2:12][NH:13][CH2:14][C:15]#[N:16])([O-:9])=[O:8].Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C(Cl)Cl>[N+:7]([C:10]1[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=1[CH2:12][N:13]([CH2:14][C:15]#[N:16])[C:22](=[O:23])[O:24][CH2:25][CH3:26])([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 59862489HCID 59862489, compound

Product 1

HCID 59862492HCID 59862492, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Pyridine (151 mg, 1.91 mmol) was added to a CH2Cl2 solution (20 mL) containing 2-(2-nitrobenzylamino)acetonitrile (1) (122 mg, 0.638 mmol). The reaction mixture was cooled to 0° C. under a nitrogen atmosphere, and ethyl chloroformate (0.182 mL, 1.914) was added dropwise. The reaction mixture was stirred at room temperature for 1 hour, and then washed with 1N HCl (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The resulting oil was purified by column chromatography (Biotage 40 m, 100% CH2Cl2) to provide 97 mg (0.37 mmol, 58% yield) of ethyl 2-nitrobenzyl(cyanomethyl)carbamate (2) as a yellow oil.

Workup

  1. washwashed with 1N HCl (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil was purified by column chromatography (Biotage 40 m, 100% CH2Cl2)

Sources & evidence

ORD record
ord-82647ab2bbce4260b9ba9d16e4f36f8d
Source dataset
uspto-grants-2012_04
Patent number
US08163738B2

Reaction notes

Loading…