Dimethylformamide → N-Methyl-N'-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

HRID 542464

반응식

HRID 542464 반응식
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.[CH3:23][N:24](C)[CH:25]=[O:26]>>[CH3:23][NH:24][C:25](=[O:26])[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

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 197942325-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride

생성물 1

HCID 13853578N-Methyl-N'-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]urea

실험 절차

5-(4-Aminophenyl)-2(1H)-pyrazinone hydrochloride (1.0 g) was suspended in dimethylformamide (30 ml) and triethylamine (1.2 ml) was added. The dark solution was filtered. Methyl isocyanate (0.53 ml) was added and the mixture was stirred for 17 hours at room temperature. The mixture was evaporated to dryness and the black residue washed with water; the insoluble material was collected by filtration and then reprecipitated from dimethylformamide solution with water. The precipitate was filtered off and the filtrate evaporated to dryness. The cream-coloured residue was collected to afford the title compound, m.p. >300° C.; C12H12N4O2Calculated: C 59.01; H 4.95; N 22.94: Found: C 59.09; H 4.94; N 22.90: νmax (liquid paraffin) 1675, 1642 cm-1 ; N.m.r. δ(DMSO-d6) 2.76 (d, 3H, CH3), 5.98 (q 1H, --NHCH3), 7.91, 8.08 (2d, 2H, pyridine H's).

후처리

  1. filtrationThe dark solution was filtered
  2. additionMethyl isocyanate (0.53 ml) was added
  3. customThe mixture was evaporated to dryness
  4. washthe black residue washed with water
  5. filtrationthe insoluble material was collected by filtration
  6. customreprecipitated from dimethylformamide solution with water
  7. filtrationThe precipitate was filtered off
  8. customthe filtrate evaporated to dryness
  9. customThe cream-coloured residue was collected

출처 및 근거

ORD 기록
ord-4027567afd2f4efd937b16b2416b5e3a
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04657906

연결된 노트

불러오는 중…