1-Bromo-3-chloropropane → HCID 13746933, compound

HRID 2290222Notes

Reaction equation

HRID 2290222 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[CH2:5][C:4](=[O:12])[NH:3][C:2]1=[O:13].CC(C)([O-])C.[K+].Br[CH2:21][CH2:22][CH2:23][Cl:24]>CN(C)C=O>[CH2:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:1][C:2](=[O:13])[N:3]([CH2:21][CH2:22][CH2:23][Cl:24])[C:4]1=[O:12]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 7405391H-3-benzazepine-2,4(3H,5H)-dioneHCID 23665647Potassium tert-butoxide

Product 1

HCID 13746933HCID 13746933, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A quantity of 3.5 gm (0.020 mol) of 1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dione is suspended in 30 ml of dimethylformamide and mixed with 2.5 gm of potassium tert.butoxide with stirring. After ten minutes, the solution obtained is added dropwise to 3.5 ml of 1-bromo-3-chloropropane in 20 ml of dimethylformamide while being cooled with ice. After one hour the mixture is poured onto ice water. A short time later the greasy precipitate crystallizes. The precipitate is subjected to suction filtration, dissolved in acetone, precipitated again with water, suction filtered, and dried.

Workup

  1. waitAfter ten minutes
  2. customthe solution obtained
  3. temperaturewhile being cooled with ice
  4. additionAfter one hour the mixture is poured onto ice water
  5. customA short time later the greasy precipitate crystallizes
  6. filtrationThe precipitate is subjected to suction filtration
  7. dissolutiondissolved in acetone
  8. customprecipitated again with water, suction
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-2bc87028fc1c404092bae02ed3455283
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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