Triethylamine → 4H-3,1-Benzoxazin-4-one, 2,2'-(2-phenylethenylidene)bis-

HRID 620767Notes

Reaction equation

[I-].ClC1C=CC=C[N+]=1C.O=[C:11]([NH:32][C:33]1[CH:41]=[CH:40][CH:39]=[CH:38][C:34]=1[C:35]([OH:37])=[O:36])[C:12](=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]([NH:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19])=[O:14].C(N(CC)CC)C>C(Cl)Cl>[CH:29]1[CH:28]=[CH:27][C:26]([CH:25]=[C:12]([C:13]2[O:14][C:18](=[O:19])[C:17]3[C:16](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:15]=2)[C:11]2[O:36][C:35](=[O:37])[C:34]3[C:33](=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:32]=2)=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Under nitrogen gas current, 2-chloro-N-methylpyridinium iodide (691 mg, 2.78 mmol) was suspensed in dry methylene chloride (5 ml) and a solution of Compound 11 (500 mg, 1.16 mmol) and dry triethylamine (0.76 ml, 5.57 mmol) in dry methylene chloride (5 ml) were added. The mixture was stirred at 40° C. for 3.5 hours. After the reaction, methylene chloride was added, and the mixture was washed with 1N.HCl, water, 4% NaHCO3 aqueous solution and water and dried over magnesium sulfate. The solvent was evaporated. The residue was crystallized rrcm isopropylether to give the desired compound 52 in crystal (410 mg, yield, 90%). m.p., IR, and NMR spectra of the product fully agreed with those of the one obtained in Example 19.

Workup

additionwas added
washthe mixture was washed with 1N
dry with materialHCl, water, 4% NaHCO3 aqueous solution and water and dried over magnesium sulfate
customThe solvent was evaporated
customThe residue was crystallized rrcm isopropylether

Sources & evidence

ORD record: ord-e8b9c8be6d674d00b5a19b089560c216
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822791

Reaction notes

Loading…