Pyridine → HCID 59862492, compound

HRID 1186104Notes

Reaction equation

HRID 1186104 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-4aee292984f64b11bc47f12e770651d1
Source dataset
uspto-grants-2014_03
Patent number
US08673898B2

Reaction notes

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