Isoamyl Nitrite → HCID 20093457, compound

HRID 373614Notes

Reaction equation

HRID 373614 reaction equation
[CH2:1]([NH:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[N:13](OCCC(C)C)=[O:14]>CCO>[CH2:1]([NH:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([CH3:12])[C:7]=1[N:13]=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 20093436HCID 20093436, compound

Product 1

HCID 20093457HCID 20093457, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5-butylamino-1,3-dimethylpyrazole (4.0 g, 23.9 mmol) in EtOH (100 mL) there was added dropwise, under nitrogen, isoamyl nitrite (35 mL) and the mixture was stirred at room temperature for 3 hours. The progress of the reaction was monitored by tlc (SiO2, developed with EtOAc/hexanes [3:2]) and when no starting material remained, the solution was evaporated to dryness. This mixture was purified by chromatography on a SiO2 column (400 mL) developed with EtOAc/hexanes (40:60). The faster components were eluted first (one of which is the isomeric N-nitroso derivative which can be isomerized with acid to yield additional product) followed by the Step C compound (3.23 g, 69%) as reddish crystals.

Workup

  1. customthe solution was evaporated to dryness
  2. customThis mixture was purified by chromatography on a SiO2 column (400 mL)
  3. washThe faster components were eluted first (one of which
  4. customto yield additional product)

Sources & evidence

ORD record
ord-de849a6330c14b4ca8933481f99cb0ca
Source dataset
uspto-grants-1992_11
Patent number
US05164407

Reaction notes

Loading…