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

HRID 53750

Reaction equation

HRID 53750 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.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:24]1CCC(N=C=NC2CCCCC2)CC1.C[N:40]([CH:42]=[O:43])C>>[C:19]1([CH3:24])[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:42]([NH:40][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:43]

Participants

5

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 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 1-carboxymethyl-1,4-dihydroquinoxaline-2,3-dione (100 mg, 0.450 mmol) and aniline (62 mg, 0.66 mmol) in dry DMF (2 mL) under N2 at 28° C., DCC (95 mg, 0.46 mmol, Aldrich) was added in one portion. The solution was stirred for 4 h at 28° C. The insoluble solid was filtered and washed with DMF (1 mL). The clear filtrate was poured into water (30 mL). The solid thus obtained was filtered and dried under vacuum (water aspirator) to yield 133 mg crude product as a grey powder. It 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 55 mg of pure (1H NMR) N-(N'-phenylcarboxamidyl)methyl-1,4-dihydroquinoxaline-2,3-dione as a white solid (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 4.92 (s, 2H), 7.01-7.30 (m, 7H), 7.51 (d, 2H, J=6.9 Hz), 10.26 (s, 1H), 12.13 (s, 1H). IR (KBr, cm-1): 3148, 1715, 1671, 1600, 1557. HRMS: Calculated for C16H3N3O3, 295.0951; Observed, 296.1033.

Workup

  1. filtrationThe insoluble solid was filtered
  2. washwashed with DMF (1 mL)
  3. additionThe clear filtrate was poured into water (30 mL)
  4. customThe solid thus obtained
  5. filtrationwas filtered
  6. dry with materialdried under vacuum (water aspirator)
  7. customto yield 133 mg crude product as a grey powder
  8. customIt was purified by Soxhlet extraction
  9. customat 120° C.
  10. waitfor 4 h
  11. customThe insoluble material (in the thimble) was dried under vacuum

Sources & evidence

ORD record
ord-ab2997d5f3a743cf9955ce38dffdac4b
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Linked notes

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