Triethylamine → HCID 86604803, compound

HRID 856156Notes

Reaction equation

HRID 856156 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[N+:10]([C:13]1[CH:26]=[CH:25][C:16]([C:17]([O:19][CH2:20][C@:21]2([CH3:24])[CH2:23][O:22]2)=[O:18])=[CH:15][CH:14]=1)([O-:12])=[O:11].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[N:3]([CH2:24][C@@:21]([OH:22])([CH3:23])[CH2:20][O:19][C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:26][CH:25]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 147239Oxiranemethanol, 2-methyl-, 4-nitrobenzoate, (2S)-HCID 178526855HCID 178526855, compound

Product 1

HCID 86604803HCID 86604803, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
62.5 °C

Procedure

2-Chloro-4-nitro-1H-imidazole (3 g, 20.34 mmol) and (S)-2-methyloxiran-2-ylmethyl 4-nitrobenzoate (5.31 g, 22.37 mmol) were dissolved in ethyl acetate (10 ml). Triethylamine (0.57 ml, 4.07 mmol) was added to the solution, and the resulting mixture was stirred at 60-65° C. for 10 hours. The reaction mixture was concentrated under reduced pressure. Ethyl acetate (3 ml) and toluene (30 ml) were added to the residue, and the resulting precipitates were filtered off to afford (S)-2-chloro-4-nitro-1-[2-hydroxy-3-(4-nitrobenzoyloxy)-2-methylpropyl]imidazole (6.82 g, yield 87%) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate (3 ml) and toluene (30 ml) were added to the residue
  3. customthe resulting precipitates
  4. filtrationwere filtered off

Sources & evidence

ORD record
ord-110b213b7e8f41b0b7b1b6666a146a53
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

Loading…