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

HRID 2290219Notes

Reaction equation

HRID 2290219 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

An amount of 0.24 gm (5.5 mmol) of sodium hydride dispersion in oil (55%) is added to 1.35 gm (5 mmol) of 7-bromo-8-methoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one in 15 ml of dimethylsulfoxide, and the mixture is stirred for 30 minutes at ambient temperature and ten minutes at 35° to 40° C. The solution is added dropwise, with stirring, to 0.79 gm (5.5 mmol) of 1-bromo-3-chloropropane in 5 ml of dimethylsulfoxide with stirring. It is then stirred for two 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. The residue is purified over a silica gel column with ethyl acetate as eluant.

Workup

  1. additionThe solution is added dropwise
  2. stirringwith stirring
  3. stirringIt is then stirred for two hours at ambient temperature
  4. additionpoured onto ice water
  5. extractionextracted four times with methylene chloride
  6. washThe methylene chloride extracts are washed several times with water
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified over a silica gel column with ethyl acetate as eluant

Sources & evidence

ORD record
ord-de95059710964dacb64f2d9c68d01e19
Source dataset
uspto-grants-1986_10
Patent number
US04616011

Reaction notes

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