Toluene → 3-chloro-1-(2,4-dimethoxybenzyl)benzo[f]quinoxalin-2(1H)-one

HRID 744021Notes

Reaction equation

[C:1]([Cl:4])(Cl)=O.C1(C)C=CC=CC=1.[CH3:12][O:13][C:14]1[CH:36]=[C:35]([O:37][CH3:38])[CH:34]=[CH:33][C:15]=1[CH2:16][N:17]1[C:26]2[C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[CH:23]=[CH:22][C:21]=2[NH:20]C(=O)[C:18]1=[O:32]>CN(C)C=O>[Cl:4][C:1]1[C:18](=[O:32])[N:17]([CH2:16][C:15]2[CH:33]=[CH:34][C:35]([O:37][CH3:38])=[CH:36][C:14]=2[O:13][CH3:12])[C:26]2[C:25]3[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=3[CH:23]=[CH:22][C:21]=2[N:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 20% phosgene in toluene (10 ml, 19 mmol) was added to a solution of 1-(2,4-dimethoxybenzyl)benzo[f]quinoxaline-2,3(1H, 4H)-dione (950 mg; 2.6 mmol) in dry N,N-dimethylformamide (100 ml) with stirring at 0° C. The mixture was stirred at room temperature overnight, and evaporated to dryness. The residue was triturated with ice/water, filtered and dried in vacuo to give 900 mg (90%) of the title compound, m.p. 186° C. 1H-NMR (DMSO-d6): δ 3.80 (s, 3H), 3.82 (s, 3H), 5.65 (s, 2H), 6.45 (dd, 1H), 6.55 (d, 1H), 7.00 (d, 1H), 7.35 (m, 1H), 7.55 (m, 1H), 7.75 (m, 2H), 7.90 (m, 1H), 8.22 (d, 1H).

Workup

stirringThe mixture was stirred at room temperature overnight
customevaporated to dryness
customThe residue was triturated with ice/water
filtrationfiltered
customdried in vacuo

Sources & evidence

ORD record: ord-019b5f0f35d64176acdca0df72abc233
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559106

Reaction notes

Loading…