Ethyl isocyanoacetate → HCID 21291405, compound

HRID 622656Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:11]2[C:12](=[O:19])[N:13]([CH3:18])[CH2:14][C:15](=O)[NH:16][C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH2:20]([O:22][C:23](=[O:27])[CH2:24][N+:25]#[C-:26])[CH3:21].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>CN(C)C=O>[CH3:18][N:13]1[C:12](=[O:19])[C:11]2=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=[CH:8][CH:9]=[C:10]2[N:16]2[CH:26]=[N:25][C:24]([C:23]([O:22][CH2:20][CH3:21])=[O:27])=[C:15]2[CH2:14]1

Participants

Conditions

Temperature: -20 °C

Procedure

6-Ethoxycarbonyl-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione (10 mmol) was dissolved in 25 ml dry dimethylformamide (DMF). While stirring, K-t-butoxide (12 mmol) was added and the mixture was thereafter cooled to -20° C. A -30° C. cold solution of K-t-butoxide (12 mmol) in dry DMF (15 ml) was charged with isocyano-acetic acid ethylester (12 mmol). This solution was added to the above mentioned solution, and the combined solution was stirred at room temperature for 2 hours. 2 ml of acetic was added, whereafter the solution was evaporated to dryness. The oily residue was subjected to SiO2 -purification with acetone/chloroform (1/3) as eluent. This yielded the title compound as a crystalline powder. M.p. 136.3°-139.9° C.

Workup

additionThis solution was added to the
stirringthe combined solution was stirred at room temperature for 2 hours
customwas evaporated to dryness

Sources & evidence

ORD record: ord-44653b57a4f34892b2fc48bdf5a0470c
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04772599

Reaction notes

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