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

HRID 54339

Reaction equation

HRID 54339 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Conditions

Temperature
28 °C

Procedure

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: δ5.02 (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.

Workup

  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

Sources & evidence

ORD record
ord-a2deecef383e4f65bc96ab62684ab91a
Source dataset
uspto-grants-1997_04
Patent number
US05622952

Linked notes

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