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

HRID 53751

반응식

HRID 53751 반응식
C(C[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])(O)=O.[N+]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([O-])=O.[CH2:27]1CCC(N=C=NC2CCCCC2)CC1.C[N:43]([CH:45]=[O:46])C>>[C:25]1([CH3:27])[CH:26]=[CH:20][CH:21]=[CH:22][C:23]=1[NH:24][C:45]([NH:43][N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7](=[O:15])[C:6]1=[O:16])=[O:46]

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 74754-NitroanilineHCID 10868DicyclohexylcarbodiimideHCID 129386642-(2,3-Dioxo-1,2,3,4-tetrahydroquinoxalin-1-yl)acetic acid

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-1,4-dihydroquinoxaline-2,3-dione (250 mg, 1.140 mmol) and p-nitroaniline (156 mg, 1.140 mmol) in DMF (3 mL) under N2 at 0° C., DCC (233 mg, 1.140 mmol) was added in one portion. The solution was allowed to warm to 28° C. and stirred at that temperature overnight. The precipitated solid was filtered and the clear filtrate was poured into water (30 mL). The solid thus obtained was filtered and dried under vacuum (water aspirator) to obtain 100 mg crude product as a yellow powder. The crude product was purified by Soxhlet extraction in boiling ethanol (20 mL), keeping the oil bath temperature at 120° C., for 4 h. The insoluble material (in the thimble) was dried under vacuum to obtain 23 mg pure (1H NMR) N-(N'-(p-nitrophenyl)carboxamidyl)methyl-1,4-dihydroquinoxaline-2,3-dione as a light yellow powder (some of the product also ends up being extracted by hot ethanol which accounts for the low yield of the pure product). M.p. >300° C. (decomposes). 1H NMR: δ 5.02 (s, 1H), 7.13-7.3 (m, 4H), 7.78 (d, 1H, J=8.4 Hz), 8.21 (d, 1H, J=8.4 Hz), 10.92 (s, 1H), 12.16 (s, 1H). IR (KBr, cm-1): 3453, 1701, 1684, 1625, 1572, 1509. HRMS: Calculated for C16H12N4O5, 340.0808; Observed, 340.0811.

후처리

  1. filtrationThe precipitated solid was filtered
  2. additionthe clear filtrate was poured into water (30 mL)
  3. customThe solid thus obtained
  4. filtrationwas filtered
  5. dry with materialdried under vacuum (water aspirator)
  6. customto obtain 100 mg crude product as a yellow powder
  7. customThe crude product was purified by Soxhlet extraction
  8. customat 120° C.
  9. waitfor 4 h
  10. customThe insoluble material (in the thimble) was dried under vacuum

출처 및 근거

ORD 기록
ord-6f1926f06f3d458fadcdb003b53121f4
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620979

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