Ethyl Acetate → HCID 18429190, compound

HRID 1280185Notes

Reaction equation

HRID 1280185 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH:7]([O:10][Si](C)(C)C)[C:8]#[N:9])([O-:3])=[O:2].CC[O:23]C(C)=O>O>[N+:1]([C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=1)[CH:7]([OH:10])[C:8]([NH2:9])=[O:23])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 87959714HCID 87959714, compound

Product 1

HCID 18429190HCID 18429190, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
115 °C

Procedure

3,5-dinitro-O-trimethylsilylmandelonitrile (5.0 g, 16.9 mmol) and BF3-acetic acid complex (30 ml) were dissolved in H2O (5 ml) at room temperature. The reaction temperature was raised to 115° C. immediately and stirred for 10 minutes. The reaction solution was then cooled to 0° C. H2O (100 ml) and EtOAc (200 ml) were added. The organic phase was washed with sat NaHCO3 (100 ml) and brine (100 ml). Drying over MgSO4 was followed by removal of solvents at reduced pressure. The residue was crystallized from isopropylacetate. The crystalline residue was left for preparative HPLC, which gave 2.2 g (54%) of 3,5-dinitromandeloamide.

Workup

  1. temperatureThe reaction solution was then cooled to 0° C
  2. washThe organic phase was washed with sat NaHCO3 (100 ml) and brine (100 ml)
  3. dry with materialDrying over MgSO4
  4. customwas followed by removal of solvents at reduced pressure
  5. customThe residue was crystallized from isopropylacetate
  6. waitThe crystalline residue was left for preparative HPLC, which

Sources & evidence

ORD record
ord-6e97802aa4f3440199146dff950650c1
Source dataset
uspto-grants-2002_09
Patent number
US06448442B1

Reaction notes

Loading…