Potassium Carbonate → 2-(7-chloro-3-(2-chlorobenzyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-1-yl)ethyl acetate

HRID 1186084Notes

Reaction equation

HRID 1186084 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[NH:6][C:7](=[O:20])[CH:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:19])[NH:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:30][CH2:31][O:32][C:33](=[O:35])[CH3:34]>CN(C)C=O.C(OCC)(=O)C>[C:33]([O:32][CH2:31][CH2:30][N:6]1[C:5]2[CH:21]=[CH:22][C:2]([Cl:1])=[CH:3][C:4]=2[C:10](=[O:11])[NH:9][CH:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]1=[O:20])(=[O:35])[CH3:34]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethane2×HCID 595943987-chloro-3-(2-chlorobenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

Product 1

HCID 670608182-(7-chloro-3-(2-chlorobenzyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-1-yl)ethyl acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 7-chloro-3-(2-chlorobenzyl)-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione (0.5 g, 1.5 mmol) in N,N-dimethylformamide (10 mL), was added powdered potassium carbonate (0.31 g, 2.2 mmol) followed by 2-bromoethylacetate (0.17 mL, 1.6 mmol). The mixture was stirred at ambient temperature overnight. After 20 hours, more 2-bromoethylacetate (0.05 mL, 0.5 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (3×50 mL), washed with brine (50 mL), dried with anhydrous sodium sulfate, decanted, and concentrated to yield crude 2-(7-chloro-3-(2-chlorobenzyl)-2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[e][1,4]diazepin-1-yl)ethyl acetate, which was used directly in the next step without further purification. MS (m/z): 421.1 (M+H)+.

Workup

  1. waitAfter 20 hours
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. washwashed with water (3×50 mL)
  5. washwashed with brine (50 mL)
  6. dry with materialdried with anhydrous sodium sulfate
  7. customdecanted
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-56ac125232e2472bb499d3e938db89a1
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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