Acetic Anhydride → HCID 69892358, compound

HRID 48347Notes

Reaction equation

HRID 48347 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[Cl:21])[CH:5]=[CH:6][C:7]1=[N:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[ClH:1].[C:22]([N:11]1[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:7]([CH:6]=[CH:5][C:4]2[CH:18]=[CH:19][C:20]([Cl:21])=[C:2]([Cl:1])[CH:3]=2)=[N:8][CH2:9][CH2:10]1)(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 69892837HCID 69892837, compound

Product 1

HCID 69892358HCID 69892358, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

50 mg (0.158 mmol) of (E)-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-benzo-1,4-diazepine were dissolved in a mixture of 0.1 ml of acetic anhydride and 1 ml of pyridine by heating to 80° C. The mixture was left to cool for 30 minutes then evaporated to dryness and the residue dissolved in water and ethyl acetate. The organic phase was dried over magnesium sulphate, filtered, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate for the elution. The product was dissolved in a solution of hydrogen chloride in ethyl acetate, evaporated to dryness and the residue dissolved in a small volume of acetone and left to crystallize. There was obtained 12 mg of (E)-1-acetyl-5-(3,4-dichlorostyryl)-2,3-dihydro-1H-1,4-benzodiazepine hydrochloride as an off-white solid. MS: m/e 358.9 [M+H]+.

Workup

  1. waitThe mixture was left
  2. temperatureto cool for 30 minutes
  3. customthen evaporated to dryness
  4. dissolutionthe residue dissolved in water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customthe residue chromatographed on silica gel
  9. washfor the elution
  10. dissolutionThe product was dissolved in a solution of hydrogen chloride in ethyl acetate
  11. customevaporated to dryness
  12. dissolutionthe residue dissolved in a small volume of acetone
  13. waitleft
  14. customto crystallize

Sources & evidence

ORD record
ord-3a1809874ceb4c3391ab71e1fb01ff82
Source dataset
uspto-grants-2004_03
Patent number
US06703387B2

Reaction notes

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