Tetrahydrofuran → 7-Bromomethyl-1-ethyl-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione

HRID 68952Notes

Reaction equation

HRID 68952 reaction equation
[Br-:1].[Li+].C1COCC1.Cl[CH2:9][C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:24][CH3:25])[C:15](=[O:23])[C:16]([CH3:22])([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:12]=2[CH:11]=1>O>[Br:1][CH2:9][C:10]1[CH:27]=[CH:26][C:13]2[N:14]([CH2:24][CH3:25])[C:15](=[O:23])[C:16]([CH3:22])([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:12]=2[CH:11]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 82050Lithium BromideHCID 70656225HCID 70656225, compound

Product 1

HCID 706571647-Bromomethyl-1-ethyl-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dioneYield 90.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Lithium bromide (0.678 g) was added to an THF solution (2.3 ml) of 7-chloromethyl-1-ethyl-3,3,5-trimethyl-1,5-dihydro-benzo[b][1,4]diazepine-2,4-dione (0.23 g), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, followed by extraction using ethyl acetate. The organic layer was dried with magnesium sulfate, and was condensed under reduced pressure to give the title compound (0.24 g) as a white solid.

Workup

  1. extractionfollowed by extraction
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. customcondensed under reduced pressure

Sources & evidence

ORD record
ord-62cee120ea9345d7bf16a51640e61347
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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