Ethyl isocyanate → HCID 135890115, compound

HRID 539886Notes

Reaction equation

HRID 539886 reaction equation
[CH2:1]([C:3]1[C:4](=[O:24])[NH:5][C:6]([C:11]2[CH:16]=[C:15]([NH:17][CH2:18][CH3:19])[CH:14]=[CH:13][C:12]=2[O:20][CH2:21][CH2:22][CH3:23])=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26]>C(O)C>[CH2:18]([N:17]([C:15]1[CH:14]=[CH:13][C:12]([O:20][CH2:21][CH2:22][CH3:23])=[C:11]([C:6]2[NH:5][C:4](=[O:24])[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH3:10])[N:7]=2)[CH:16]=1)[C:28]([NH:27][CH2:25][CH3:26])=[O:29])[CH3:19]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 135890119HCID 135890119, compound

Product 1

HCID 135890115HCID 135890115, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The compound (0.33 g, 1 mmol) of example 195 was dissolved in ethanol (10 ml), and added with ethyl isocyanate (0.8 g, 1.1 mmol). After refluxed for 1 h, the reaction mixture was concentrated to dryness. The resultant solid was recrystallized from ethyl acetate-petroleum ether to obtain the title compound (0.32 g, yield: 80%). 1H NMR (DMSO-d6) δ: 11.81 (1H, br), 7.58 (1H, d), 7.30 (1H, dd), 7.19 (1H, d), 5.65 (1H, t), 4.07 (2H, t), 3.55 (2H, q), 3.00 (2H, m), 2.56 (2H, q), 2.46 (2H, q), 1.77 (2H, m), 1.18 (3H, t), 1.04 (3H, t), 0.99 (3H, t), 0.98 (3H, t), 0.95 (3H, t).

Workup

  1. temperatureAfter refluxed for 1 h
  2. concentrationthe reaction mixture was concentrated to dryness
  3. customThe resultant solid was recrystallized from ethyl acetate-petroleum ether

Sources & evidence

ORD record
ord-9298cac5cd1c415ca99b03f0b619dda8
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

Loading…