Water → HCID 13309879, compound

HRID 2291265Notes

Reaction equation

C(OP(Cl)(OCC)=O)C.[CH3:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][C:13](=O)[C:12]1=[O:22].[N+:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])#[C-:24].O>CN(C)C=O>[CH3:10][N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]2[CH:24]=[N:23][C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:13]2[C:12]1=[O:22]

Participants

Conditions

Temperature: -30 °C

Procedure

6.2 ml of diethylchlorophosphate was added to a mixture of 5.3 g of 1,2,3,4-tetrahydro-1-methyl-2,3-dioxo-quinoxaline and of 4.5 g of K-t-butoxide in 50 ml dimethyl formamide (DMF) at room temperature. The resulting mixture was heated until it formed a solution and was then cooled to -30° C. A -30° C. cold mixture of 4.8 g of K-t-butoxide and 4.5 ml of ethyl isocyanoacetate in 20 ml of dry DMF was added to this solution. The resulting mixture was stirred for one hour at room temperature. Then 100 ml of water was added and the mixture was filtered. The resulting residue was crystallized leaving 2.5 g of the title compound. M.p. 218.5°-219.8° C.

Workup

temperatureThe resulting mixture was heated until it
customformed a solution
additionwas added to this solution
filtrationthe mixture was filtered
customThe resulting residue was crystallized

Sources & evidence

ORD record: ord-7a72c2561c3341f1bb0cdda44703aad0
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04795749

Reaction notes

Loading…