Acetonitrile → 7-(2-Chloroethoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 69052

Reaction equation

[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:4]1=2)[CH3:2].C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:30][CH2:31][Cl:32]>O>[Cl:32][CH2:31][CH2:30][O:19][C:16]1[CH:17]=[CH:18][C:4]2[N:3]([CH2:1][CH3:2])[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]=2[CH:15]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (1.2 g) and potassium carbonate (0.95 g) were added to 50% hydrous acetonitrile (24 ml). The mixture was heated to 70° C. to be dissolved. 1-Bromo-2-chloroethane (1.9 ml) was added, and the mixture was heated under reflux for 7 hours. The reaction mixture was cooled to room temperature. Water was added thereto, followed by extraction by ethyl acetate. The organic layer was dried by sodium sulfate, and condensed under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1). The purified product was condensed to dryness under reduced pressure to give the title compound (1.4 g) as a colorless oily matter.

Workup

dissolutionto be dissolved
temperaturethe mixture was heated
temperatureunder reflux for 7 hours
temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction by ethyl acetate
dry with materialThe organic layer was dried by sodium sulfate, and condensed under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1)
customcondensed to dryness under reduced pressure

Sources & evidence

ORD record: ord-dc5f44baa43445b6a7c5c00cf1c78cc6
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822453B2

Linked notes

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