1,2-Dichloroethane → HCID 86755859, compound

HRID 1955079Notes

Reaction equation

HRID 1955079 reaction equation
ON[C:3]([CH2:5][N:6]([CH2:20]C(C)C)[C:7](=[O:19])[CH2:8][CH:9]([CH2:15]C(C)C)[C:10]([N:12](C)C)=[O:11])=[O:4].CN1CCOCC1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH2:45]([O:52]N)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C=O)C>[CH2:45]([O:52][C:3]([CH2:5][N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH:9]([CH3:15])[C:10]([NH2:12])=[O:11])=[O:4])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 102313O-BenzylhydroxylamineHCID 54085683HCID 54085683, compound

Product 1

HCID 86755859HCID 86755859, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

N4 -(Hydroxycarbamoyl-methyl)-2,N4 -diisobutyl-N1,N1 -dimethyl-succinamide (1.30 g, 0.0041 mol) was dissolved in DMF (10 ml) and treated at 0° C. with NMM (0.56 g, 0.0041 mol) followed by EDC (0.95 g, 0.005 mol) and HOBt (0.67 g, 0.005 mol). The reaction mixture was allowed to stir at 0° C. for 20 minutes and then at ambient temperature for 2 hours before O-benzylhydroxylamine (0.76 g, 0.0062 mol) was added. The reaction mixture was allowed to stir at room temperature for a further 1.5 hours. The solvent was removed under reduced pressure and the resulting crude oil was taken up in ethyl acetate (100 ml). The solution was washed consecutively with saturated aqueous NaHCO3, 1M HCl and brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to a crude oil. The crude oil was purified by flash chromatography (silica gel, gradient elution with 5% to 10% methanol in dichloromethane) to give the title compound as a white solid (0.49 g, 29%). 1H NMR: δ(CD3OD), 7.38-7.21 (5H, br m). 4.75 (2H, s), 4.11-3.65 (2H, br m), 3.25 (1H, br m), 3.17-2.97 (2H, br m), 3.07 (3H, s), 2.81 (3H, s), 2.79-2.24 (2H, br m), 1.75 (1H, br m), 1.55-1.25 (3H, br m) and 0.91-0.64 (12H, br m).

Workup

  1. stirringto stir at room temperature for a further 1.5 hours
  2. customThe solvent was removed under reduced pressure
  3. washThe solution was washed consecutively with saturated aqueous NaHCO3, 1M HCl and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo to a crude oil
  7. customThe crude oil was purified by flash chromatography (silica gel, gradient elution with 5% to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ea3a73b7d6ac4589a4b081b3ae390371
Source dataset
uspto-grants-2000_09
Patent number
US06124329

Reaction notes

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