1-Bromo-3-chloropropane → HCID 13520688, compound

HRID 1380859Notes

Reaction equation

HRID 1380859 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:15]([O:16][CH3:17])=[CH:14][C:7]2[CH2:8][C:9](=[O:13])[NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1.Br[CH2:19][CH2:20][CH2:21][Cl:22]>CS(C)=O>[Br:3][C:4]1[C:15]([O:16][CH3:17])=[CH:14][C:7]2[CH2:8][C:9](=[O:13])[N:10]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 13520687HCID 13520687, compound

Product 1

HCID 13520688HCID 13520688, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

First, 55% sodium hydride dispersion in oil (0.24 g, 5.5 mmol) is added to 7-bromo-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepine-2-one (1.35 g, 5 mmol) in dimethylsulphoxide (15 ml) and the mixture is stirred for 10 minutes at 35°-40° C. The solution is added dropwise to 1-bromo-3-chloropropane (0.79 g, 5.5 mmol) in dimethylsulphoxide (5 ml), with stirring. Then the mixture is stirred for 2 hours at ambient temperature, poured onto ice water and extracted four times with methylene chloride. The methylene chloride extracts are washed several times with water, dried and concentrated in vacuo.

Workup

  1. stirringwith stirring
  2. stirringThen the mixture is stirred for 2 hours at ambient temperature
  3. additionpoured onto ice water
  4. extractionextracted four times with methylene chloride
  5. washThe methylene chloride extracts are washed several times with water
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a7036296f8246c4bf1aea3ba29349c0
Source dataset
uspto-grants-1986_04
Patent number
US04584293

Reaction notes

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