Sodium Sulfate → HCID 21072526, compound

HRID 1372938Notes

Reaction equation

HRID 1372938 reaction equation
[CH:1]1[C:11]2[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[CH2:8][C:7](=[O:16])[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH:19]1([CH2:22]Br)[CH2:21][CH2:20]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>CN(C)C=O.ClCCl.O>[CH:19]1([CH2:22][N:6]2[C:7](=[O:16])[CH2:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[C:11]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)[CH2:21][CH2:20]1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 113677988-Azatricyclo[9.4.0.0,2,7]pentadeca-1(15),2,4,6,11,13-hexaen-9-one

Product 1

HCID 21072526HCID 21072526, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.5 g (2.4 mmol) of 5H,7H-dibenzo[b,d]azepin-6-one in 6 ml of dimethylformamide at room temperature 0.143 g (3.58 mmol) of sodium hydride was added. After stirring for 1 hour at 60° C. 0.97 g (7.2 mmol) of cyclopropylmethyl bromide were added and stirring was continued at 60° C. overnight. After cooling to room temperature the mixture was was distributed between water and dichloromethane. The combined organic layers were reextracted with sodium sulphate solution and dried (MgSO4). After concentration in vacuo the residue was purified by column chromatography (hexane/ethyl acetate=1:1) to yield 0.6 g (95%) of 5-cyclopropylmethyl-5H,7H-dibenzo[b,d]azepin-6-one as a white crystalline compound.

Workup

  1. stirringstirring
  2. waitwas continued at 60° C. overnight
  3. temperatureAfter cooling to room temperature the mixture
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentration in vacuo the residue
  6. customwas purified by column chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-93105fb8c2a04ba9b017a5c5e3ef4778
Source dataset
uspto-grants-2007_01
Patent number
US07160875B2

Reaction notes

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