Sodium Hydroxide → (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid

HRID 48351Notes

Reaction equation

HRID 48351 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH:7]=[CH:8][C:9]1=[N:10][CH2:11][CH2:12][N:13]([CH2:20][C:21]([O:23]CC)=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2>C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][C:28]=1[Cl:29])[CH:7]=[CH:8][C:9]1=[N:10][CH2:11][CH2:12][N:13]([CH2:20][C:21]([OH:23])=[O:22])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585818ethyl (E)-2-[5-(3,4-dichlorostyryl)-2,3-dihydro-1,4-benzodiazepin-1-yl]acetate

Product 1

HCID 69892105(E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acidYield 83.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 ml of 1M sodium hydroxide solution were added to a solution of 113 mg (0.28 mmol) of ethyl (E)-2-[5-(3,4-dichlorostyryl)-2,3-dihydro-1,4-benzodiazepin-1-yl]acetate in 3 ml of ethanol and the mixture left at room temperature for 1.5 hours. The solvent was removed by evaporation and the residue dissolved in water and washed with diethyl ether. The aqueous layer was acidified with acetic acid and a red gum separated out. The gum was dissolved in a small amount of ethanol and diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulphate, filtered and evaporated to dryness to give 88 mg of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine-1-acetic acid as a red solid. MS: m/e 374.9 [M+H]+.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue dissolved in water
  3. washwashed with diethyl ether
  4. customa red gum separated out
  5. dissolutionThe gum was dissolved in a small amount of ethanol
  6. additiondiluted with ethyl acetate
  7. washwashed with water
  8. dry with materialThe organic phase was dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-363cbce40e864b21981a7c63838d8f75
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

Loading…