1,4-Dibromobutane → HCID 18328170, compound

HRID 635191Notes

Reaction equation

HRID 635191 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:12][CH:11]=[C:10]([CH3:13])[NH:9][C:8](=[O:14])[C:7]=2[CH:15]=1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].[Cl:28]N1C(=O)CCC1=O>CC(C)=O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][N:9]1[C:8](=[O:14])[C:7]2[CH:15]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[O:12][CH:11]=[C:10]1[CH2:13][Cl:28]

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 31398ChlorosuccinimideHCID 18327908HCID 18327908, compound

Product 1

HCID 18328170HCID 18328170, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2.1 g of 4,5-dihydro-7-methoxy-3-methyl-1,4-benzoxazepin-5-one was dissolved in 50 ml of acetone, 5.5 g (2.5 equivalents) of 1,4-dibromobutane and 3.5 g (2.5 equivalents) of potassium carbonate were added, then the resultant mixture was heated and refluxed for 10 hours. This was allowed to cool, then was filtered, the filtrate was concentrated, and the residue was dissolved in 60 ml of carbon tetrachloride. 1.6 g (1.2 equivalents) of N-chlorosuccinimide was added and the resultant mixture was agitated at 90° C. for minutes 15 minutes. This was allowed to cool, then was filtered, the filtrate was concentrated, water was added, and extraction was performed by methylene chloride. The methylene chloride extract was washed with water and saturated saline and was dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant crude product was refined with silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain the above-referenced compound in an amount of 1.4 g (yield of 37%).

Workup

  1. temperaturerefluxed for 10 hours
  2. temperatureto cool
  3. filtrationwas filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionthe residue was dissolved in 60 ml of carbon tetrachloride
  6. temperatureto cool
  7. filtrationwas filtered
  8. concentrationthe filtrate was concentrated
  9. additionwater was added
  10. extractionextraction
  11. extractionThe methylene chloride extract
  12. washwas washed with water and saturated saline
  13. dry with materialwas dried with anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off
  15. customto obtain the above-referenced compound in an amount of 1.4 g (yield of 37%)

Sources & evidence

ORD record
ord-73f6430aa41b448cbe49292b3217bc72
Source dataset
uspto-grants-2001_02
Patent number
US06187769B1

Reaction notes

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