Propionamide → Ethyl isocyanate

HRID 542465

Reaction equation

HRID 542465 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.C(N)(=O)CC.[NH:28]1[CH:33]=[CH:32]N=C[C:29]1=[O:34]>CN(C)C=O>[CH2:14]([N:13]=[C:12]=[O:15])[CH3:9].[CH2:33]([NH:28][C:29](=[O:34])[NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:8]=1)[CH3:32]

Participants

7

Reactant 4

HCID 6578PropionamideHCID 8471TriethylamineHCID 727581,2-Dihydropyrazin-2-oneHCID 197942325-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride

Product 2

HCID 8022Ethyl isocyanateHCID 13853579N-Ethyl-N'-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

5-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride (1.5 g) was suspended in dimethylformamide (20 ml) and triethylamine (3 ml) was added. The dark solution was filtered. Ethyl isocyanate (0.53 ml) was prepared by slowly adding lead tetra acetate (7.3 g) to a solution of propionamide (1.2 g) in dimethylformamide (50 ml). The solution was initially blood-red, but after stirring for one hour at room temperature it turned colourless. The solution of pyrazinone was added and the mixture stirred at room temperature for 36 hours. It was evaporated to dryness and the residue was washed with water; the resulting orange solid was collected by filtration. Recrystallization from glacial acetic acid afforded the title compound; m.p. >300° C.; νmax (liquid paraffin) 1660, 1640 cm-1 ; δ (DMSO-d6) 1.07 (t, 3H, CH3), 6.05 (t, 1H, --NHEt), 7.93, 8.08 (2d, 2H, pyridine H's).

Workup

  1. filtrationThe dark solution was filtered
  2. stirringthe mixture stirred at room temperature for 36 hours
  3. customIt was evaporated to dryness
  4. washthe residue was washed with water
  5. filtrationthe resulting orange solid was collected by filtration
  6. customRecrystallization from glacial acetic acid

Sources & evidence

ORD record
ord-f806cdb2a6044250a09221ef9eec01a9
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Linked notes

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