Cyanide → 6-cyano-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5(1H)-dione

HRID 1252672Notes

Reaction equation

[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10](Br)=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1.[C-:16]#[N:17].[Na]>CN(C)C=O.O>[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[C:10]([C:16]#[N:17])=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4](=[O:15])[CH2:3]1

Participants

Conditions

Temperature: 110 °C

Procedure

2.3 g of 3,4-dihydro-4-methyl-6-bromo-2H-1,4-benzodiazepine-2,5(1H)-dione (U.S. Pat. No. 4,352,817 ex.9) and 1.26 g of cupro cyanide was dissolved in 5 ml dimethyl formamide. This mixture was heated to 110° C. for 30 minutes. This mixture was then cooled to 50° C. and 2.4 g sodium in 6 ml water was added. The resulting mixture was then stirred for 10 minutes, whereafter 30 ml water was added. This mixture was extracted two times with 25 ml ethyl acetate. The organic phase was dryed with calcium chloride. After filtration the organic solution was evaporated in vacuo to give 0.78 g of the title compound. M.p. 261°-69° C.

Workup

temperatureThis mixture was then cooled to 50° C.
extractionThis mixture was extracted two times with 25 ml ethyl acetate
filtrationAfter filtration the organic solution
customwas evaporated in vacuo

Sources & evidence

ORD record: ord-459d66bb8b9840b7ada7ba9a55832fb2
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04745112

Reaction notes

Loading…