Potassium cyanate → N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

HRID 542463

Reaction equation

HRID 542463 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.[O-:16][C:17]#[N:18].[K+]>O.CN(C)C1C=CN=CC=1>[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)[C:17]([NH2:18])=[O:16]

Participants

5

Reactant 2

HCID 11378442Potassium cyanateHCID 197942325-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride

Product 1

HCID 13853577N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

5-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride (1.0 g) was dissolved in water (25 ml), to which solution potassium cyanate (0.4 g) and 4-dimethylaminopyridine (about 0.005 g) were added. The mixture was stirred at room temperature for 18 hours and the resulting suspended material collected by filtration. This was washed in hot dimethylformamide (30 ml), the insoluble material being collected and washed with water to afford the title compound, m.p. >300° C.; n.m.r. δ (DMSO-d6) 5.90 (s, 2H, --CONH2), 7.98, 8.10 (2d, 2H, pyridine H's); ν (liquid paraffin) 1710, 1665 cm-1.

Workup

  1. additionwere added
  2. filtrationcollected by filtration
  3. washThis was washed in hot dimethylformamide (30 ml)
  4. customthe insoluble material being collected
  5. washwashed with water

Sources & evidence

ORD record
ord-d5b7d78fdc07470980cafc7d40871642
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Linked notes

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