Sodium hydride → HCID 20362657, compound

HRID 1679362Notes

Reaction equation

HRID 1679362 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:16]=[CH:15][C:7]2[CH2:8][CH:9]([CH3:14])[C:10](=[O:13])[NH:11][CH2:12][C:6]=2[CH:5]=1.[CH2:17]([O:19][CH2:20][C:21](Cl)=[O:22])[CH3:18]>CN(C)C=O>[Cl:3][C:4]1[CH:16]=[CH:15][C:7]2[CH2:8][CH:9]([CH3:14])[C:10](=[O:13])[N:11]([C:21](=[O:22])[CH2:20][O:19][CH2:17][CH3:18])[CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 84189Ethoxyacetyl chlorideHCID 20362667HCID 20362667, compound

Product 1

HCID 20362657HCID 20362657, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

0.018 moles of sodium hydride is added slowly, with stirring, to a solution of 3.4 g. (0.016 moles) of 8-chloro-4-methyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one in 60 ml. of dimethylformamide. The reaction mixture is heated to 80° C. for 15 minutes and then cooled in an ice bath. While cooling, 2.2 g. (0.018 moles) of ethoxyacetyl chloride are added dropwise and then the reaction mixture is gradually brought to a temperature of 80° C. and maintained at this temperature for 3 hours. The reaction mixture is then cooled, evaporated to dryness in vacuo and the residue extracted with chloroform. The organic solution is washed twice with water, dried over anhydrous sodium sulfate, filtered and then evaporated to dryness in vacuo. The residual solid is purified by chromatography on a silica column, using a mixture of benzene/ethanol (9:1 v/v) as eluent, and it is then recrystallized from 2-propanol. 2.5 g. (52% of theory) of 8-chloro-2-(ethoxyacetyl)-4-methyl-1,2,4,5-tetrahydro- 3H-2-benzazepin-3-one are obtained. M.P. 123°-124° C.

Workup

  1. temperaturecooled in an ice bath
  2. temperatureWhile cooling
  3. customis gradually brought to a temperature of 80° C.
  4. temperaturemaintained at this temperature for 3 hours
  5. temperatureThe reaction mixture is then cooled
  6. customevaporated to dryness in vacuo
  7. extractionthe residue extracted with chloroform
  8. washThe organic solution is washed twice with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customevaporated to dryness in vacuo
  12. customThe residual solid is purified by chromatography on a silica column
  13. additiona mixture of benzene/ethanol (9:1 v/v) as eluent
  14. customit is then recrystallized from 2-propanol

Sources & evidence

ORD record
ord-e5c1ccd6dac3480b844d478bc303fd8e
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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