Aniline → 1-[[(o-Tolylamino)carbonyl]amino]-1,4-dihydro-2,3-quinoxalinedione

HRID 53753

반응식

HRID 53753 반응식
C(C[N:5]1[C:14]2[C:9](=[CH:10][C:11](Br)=[C:12](Br)[CH:13]=2)[NH:8][C:7](=[O:17])[C:6]1=[O:18])(O)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:26]1CCC(N=C=NC2CCCCC2)CC1.C[N:42]([CH:44]=[O:45])C>>[C:21]1([CH3:26])[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][C:44]([NH:42][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:17])[C:6]1=[O:18])=[O:45]

참가 물질

5

반응물 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 199585561-Carboxymethyl-6,7-dibromo-1,4-dihydroquinoxaline-2,3-dione

생성물 1

HCID 199585841-[[(o-Tolylamino)carbonyl]amino]-1,4-dihydro-2,3-quinoxalinedione

반응 조건

온도
28 °C

실험 절차

To a stirred solution of N-carboxymethyl-6,7-dibromo-1,4-dihydroquinoxaline-2,3-dione (100 mg, 0.250 mmol) and aniline (25 mg, 0.25 mmol) in dry DMF (1.5 mL) under N2 at 28° C., DCC (55 mg, 0.25 mmol) was added in one portion. The solution was stirred at 28° C. for 18 h. The insoluble white solid was filtered and the clear filtrate was poured into water (6 mL). The precipitated solid was filtered and air dried to obtain 113 mg crude product as a grey powder. The crude product was then purified by Soxhlet extraction in boiling ethanol (20 mL), keeping the oil bath temperature at 120° C., for 5 h. The residue (in the thimble) was dried in the oven (approx. 70°-80° C.) overnight to furnish 35 mg pure (1H NMR) N-(N'-phenylcarboxamidyl)methyl-6,7-dibromo-1,4-dihydroquinox-aline-2,3-dione as a light grey powder; m.p. >300° C. (decomposes). 1H NMR: δ 4.97 (s, 1H), 6.99-7.11 (m, 1H), 7.23-7.37 (m, 2H), 7.44 (s, 1H), 7.52 (d, 2H, J=8.4 Hz), 7.73 (s, 1H), 10.25 (s, 1H), 12.25 (s, 1H). IR (KBr, cm-1): 3620, 3468, 1714, 1694, 1595, 1542. HRMS: Calculated for C16H11Br2N3O3, 450.9168; Observed, 450.9177.

후처리

  1. filtrationThe insoluble white solid was filtered
  2. additionthe clear filtrate was poured into water (6 mL)
  3. filtrationThe precipitated solid was filtered
  4. customair dried
  5. customto obtain 113 mg crude product as a grey powder
  6. customThe crude product was then purified by Soxhlet extraction
  7. customat 120° C.
  8. waitfor 5 h
  9. customThe residue (in the thimble) was dried in the oven (approx. 70°-80° C.) overnight

출처 및 근거

ORD 기록
ord-f353e0c4d077491b84d0174268e2ebf0
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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