Isoamyl Nitrite → HCID 53629138, compound

HRID 1926762Notes

Reaction equation

HRID 1926762 reaction equation
N[C:2]1[S:3][C:4]([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:5][N:6]=1.C(ON=O)CC(C)C>C1COCC1>[S:3]1[C:4]([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][C:9]2=[O:13])=[CH:5][N:6]=[CH:2]1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 15979797HCID 15979797, compound

Product 1

HCID 53629138HCID 53629138, compoundYield 32.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 250 ml, three-necked flask fitted with a magnetic stirrer and reflux condenser under inert atmosphere, 1-[(2-amino-1,3-thiazol-5-yl)methyl]pyrrolidin-2-one 248 (1.04 g, 6.8 mmol) is dissolved in THF 20 ml). Isoamylnitrite (1.59 g, 13.6 mmol) is added and the mixture is heated at reflux for 3 h. The solvent is evaporated and the residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/5 (v/v)) to give 405 mg of 1-(1,3-thiazol-5-ylmethyl)pyrrolidin-2-one 249.

Workup

  1. customIn a 250 ml, three-necked flask fitted with a magnetic stirrer
  2. temperaturethe mixture is heated
  3. temperatureat reflux for 3 h
  4. customThe solvent is evaporated
  5. customthe residue is purified by chromatography on silicagel (CH2Cl2/MeOH: 95/5 (v/v))

Sources & evidence

ORD record
ord-e36de3a0834b4d0ba07bfb180ec621a3
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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