Tert-Butyl nitrite → Ethyl 2-(2-cyanothiazol-4-yl)acetate

HRID 524643Notes

Reaction equation

HRID 524643 reaction equation
N(OC(C)(C)C)=O.[C:8]([Cu])#[N:9].N[C:12]1[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1>C(#N)C>[C:8]([C:12]1[S:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:16]=1)#[N:9]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 90043492Ethyl 2-(2-cyanothiazol-4-yl)acetateYield 25.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a mixture of tert-butyl nitrite (10 mL, 80 mmol) and CuCN (7.28 g, 80 mmol) in anhydrous acetonitrile (30 mL) was added a solution of ethyl 2-(2-aminothiazol-4-yl)acetate (7.5 g, 40 mmol) in anhydrous acetonitrile (20 mL) dropwise over a period of 1 hour at 50° C., then the mixture was stirred at the temperature for 2.5 hours. The mixture was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=25/1) to give the title compound as yellowish liquid (2 g, 25%). The compound was characterized by the following spectroscopic data:

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=25/1)

Sources & evidence

ORD record
ord-b03a18e286974f3bba62610e8e1360a1
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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