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

HRID 648968Notes

Reaction equation

HRID 648968 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

Here, 1,3,4,5-tetrahydro-2H-3-benzazepin-2,4-dione (3.5 g, 0.020 mol) is suspended in dimethylformamide (30 ml) and potassium tert. butoxide (2.5 g) is added with stirring. After 10 minutes the resulting solution is added dropwise, while cooling with ice, to 1-bromo-3-chloro-propane (3.5 ml) in dimethylformamide (20 ml). After one hour it is poured onto ice water. After a short time the greasy precipitate crystallizes. The precipitate is suction filtered, dissolved in acetone, reprecipitated with water, suction filtered and dried.

Workup

  1. additionAfter 10 minutes the resulting solution is added dropwise
  2. additionAfter one hour it is poured onto ice water
  3. customAfter a short time the greasy precipitate crystallizes
  4. filtrationfiltered
  5. dissolutiondissolved in acetone
  6. customreprecipitated with water, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-fa7139568d4244faa1a3560c0fc043e9
Source dataset
uspto-grants-1988_04
Patent number
US04737495

Reaction notes

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